Category: 10378-06-0

Bovin, N. V. published the artcileIsomerization of (trifluoroacetamido)propyl 2-acetamido-2-deoxy-β-D-galactopyranoside into an α-anomer. A facile synthesis of artificial T-antigen, Safety of (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, the publication is Bioorganicheskaya Khimiya (1986), 12(4), 533-8, database is CAplus and MEDLINE.

β-Glycoside I [R = O(CH₂)₃NHAc, R¹ = H], prepared by glycosidation of I (R = H, R¹ = Cl) with HO(CH₂)₃NHAc in the presence of Hg(CN)₂, was isomerized by BF₃.Et₂O to give 50-60% α-anomer I [R = H, R¹ = O(CH₂)₃NHAc] (II) and oxazoline III. α-Anomer II was converted to benzylidene derivative IV (R = H) which was glycosidated by acetobromogalactose to give 50% IV (R = 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl), followed by deacetylation to give bioside V, the precursor for artificial T-antigen.

Bioorganicheskaya Khimiya published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Safety of (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Prakash, Thazha P. published the artcileComprehensive Structure-Activity Relationship of Triantennary N-Acetylgalactosamine Conjugated Antisense Oligonucleotides for Targeted Delivery to Hepatocytes, Quality Control of 10378-06-0, the publication is Journal of Medicinal Chemistry (2016), 59(6), 2718-2733, database is CAplus and MEDLINE.

The comprehensive structure-activity relationships of triantennary GalNAc conjugated ASOs for enhancing potency via ASGR mediated delivery to hepatocytes is reported. Seventeen GalNAc clusters were assembled from six distinct scaffolds and attached to ASOs. The resulting ASO conjugates were evaluated in ASGR binding assays, in primary hepatocytes, and in mice. Five structurally distinct GalNAc clusters were chosen for more extensive evaluation using ASOs targeting SRB-1, A1AT, FXI, TTR, and ApoC III mRNAs. GalNAc-ASO conjugates exhibited excellent potencies (ED₅₀ 0.5-2 mg/kg) for reducing the targeted mRNAs and proteins. This work culminated in the identification of a simplified tris-based GalNAc cluster (THA-GN3), which can be efficiently assembled using readily available starting materials and conjugated to ASOs using a solution phase conjugation strategy. GalNAc-ASO conjugates thus represent a viable approach for enhancing potency of ASO drugs in the clinic without adding significant complexity or cost to existing protocols for manufacturing oligonucleotide drugs.

Journal of Medicinal Chemistry published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Quality Control of 10378-06-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Saneyoshi, Hisao published the artcileConjugatable and Bio-reduction Cleavable Linker for the 5′-Functionalization of Oligonucleotides, SDS of cas: 10378-06-0, the publication is Journal of Organic Chemistry (2017), 82(3), 1796-1802, database is CAplus and MEDLINE.

An efficient conjugate and bioreduction cleavable linker was designed and synthesized for the 5′-terminal ends of oligonucleotides. A phosphoramidite reagent bearing this linker was successfully applied to solid phase synthesis and incorporated at the 5′-terminal ends of oligonucleotides. The controlled pore glass (CPG)-supported oligonucleotides were subsequently conjugated to a diverse range of functional mols. using a CuAAC reaction. The synthesized oligonucleotide conjugates were then cleaved using a nitroreductase/NADH bioreduction system to release the naked oligonucleotides.

Journal of Organic Chemistry published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, SDS of cas: 10378-06-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Nair, Jayaprakash K. published the artcileMultivalent N-Acetylgalactosamine-Conjugated siRNA Localizes in Hepatocytes and Elicits Robust RNAi-Mediated Gene Silencing, Application In Synthesis of 10378-06-0, the publication is Journal of the American Chemical Society (2014), 136(49), 16958-16961, database is CAplus and MEDLINE.

Conjugation of small interfering RNA (siRNA) to an asialoglycoprotein receptor ligand derived from N-acetylgalactosamine (GalNAc) facilitates targeted delivery of the siRNA to hepatocytes in vitro and in vivo. The ligands derived from GalNAc are compatible with solid-phase oligonucleotide synthesis and deprotection conditions, with synthesis yields comparable to those of standard oligonucleotides. S.c. (SC) administration of siRNA-GalNAc conjugates resulted in robust RNAi-mediated gene silencing in liver. Refinement of the siRNA chem. achieved a 5-fold improvement in efficacy over the parent design in vivo with a median ED (ED₅₀) of 1 mg/kg following a single dose. This enabled the SC administration of siRNA-GalNAc conjugates at therapeutically relevant doses and, importantly, at dose volumes of ≤1 mL. Chronic weekly dosing resulted in sustained dose-dependent gene silencing for over 9 mo with no adverse effects in rodents. The optimally chem. modified siRNA-GalNAc conjugates are hepatotropic and long-acting and have the potential to treat a wide range of diseases involving liver-expressed genes.

Journal of the American Chemical Society published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Application In Synthesis of 10378-06-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Yamazaki, Tatsumi published the artcileAmino sugars. 127. The synthesis of uridine diphosphate N-acetylhexosamines and uridine 5′-(2-acetamido-2-deoxy-α-D-mannopyranosyluronic acid diphosphate), Formula: C14H19NO8, the publication is Canadian Journal of Chemistry (1981), 59(15), 2247-52, database is CAplus.

2-Methyl-(2-acetamido-3,4,6-trio-O-acetyl-1,2-dideoxy-β-D-mannopyrano)-[2,1-d]-2-oxazoline was efficiently converted into 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranosyl phosphate (I), by treatment with dibenzyl phosphate, followed by catalytic hydrogenolysis of the benzyl groups. Similarly, 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl phosphate and -galactopyranosyl phosphate were synthesized from the resp. peracetyl oxazolines. In each case, the procedures for preparing the oxazoline, and conversion into the glycosyl phosphate, were modified to give high yields of pure products. I was coupled with 2′,3′-di-O-acetyluridine 5′-monophosphate by a modification of the mixed anhydride procedure, to give 2′,3′-di-O-acetyluridine 5′-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-mannopyranosyl diphosphate), which was readily purified by preparative TLC and O-deacetylated to give uridine diphosphate N-acetylmannosamine (II) in high yield. Similarly, uridine 5′-(2-acetamido-2-deoxy-α-D-glucopyranosyl- and -galactopyranosyl diphosphates) were synthesized by rapid, efficient procedures, not involving ion-exchange chromatog. II was converted into mannopyranosyluronic acid III, required for biosynthetic studies, without the preparation of a special Pt catalyst. All the synthetic uridine diphosphate sugars were characterized by optical rotation, ¹H NMR spectrum, and elemental anal.

Canadian Journal of Chemistry published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C25H34N4O2S, Formula: C14H19NO8.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Clark, Matthew A. published the artcileOxidation of bicyclic oxazolines: applications to glycomimetics and novel saccharide derivatives, Related Products of esters-buliding-blocks, the publication is Tetrahedron Letters (2002), 43(3), 347-349, database is CAplus.

A general procedure is reported for the oxidation of substituted oxazolines to α-acyloxyketoximes and the derived α-acyloxyketones. In the case of oxazolines derived from 2-acetamido-2-deoxyhexoses, the resulting 2-oximinoesters can be converted to 2-nitroglycals.

Tetrahedron Letters published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Related Products of esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Rensen, Patrick C. N. published the artcileDesign and Synthesis of Novel N-Acetylgalactosamine-Terminated Glycolipids for Targeting of Lipoproteins to the Hepatic Asialoglycoprotein Receptor, COA of Formula: C14H19NO8, the publication is Journal of Medicinal Chemistry (2004), 47(23), 5798-5808, database is CAplus and MEDLINE.

A novel glycolipid has been prepared that contains a cluster glycoside with an unusually high affinity for the asialoglycoprotein receptor (ASGPr) and a bile acid moiety that mediates stable incorporation into lipidic particles. The glycolipid spontaneously associated with low-d. lipoproteins (LDL) and high-d. lipoproteins (HDL) within human and murine plasma, and loading of lipoproteins with this glycolipid resulted in an efficient dose-dependent recognition and uptake of LDL and HDL by the liver (and not by spleen) upon i.v. injection into wild-type mice. Preinjection with asialoorosomucoid largely inhibited the uptake, establishing that both HDL and LDL were selectively recognized and processed by the ASGPr on liver parenchymal cells. Finally, repeated i.v. administration of the glycolipid to hyperlipidemic LDL receptor-deficient mice evoked an efficient and persistent cholesterol-lowering effect. These results indicate that the glycolipid may be a promising alternative for the treatment of hyperlipidemic patients who do not respond sufficiently to current cholesterol-lowering therapies.

Journal of Medicinal Chemistry published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, COA of Formula: C14H19NO8.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Valentijn, A. Rob P. M. published the artcileSolid-phase synthesis of lysine-based cluster galactosides with high affinity for the asialoglycoprotein receptor, Related Products of esters-buliding-blocks, the publication is Tetrahedron (1997), 53(2), 759-770, database is CAplus.

Structurally well defined di- and tri-antennary lysine-based galactose- and N-acetylgalactosamine-containing ligands for the hepatic asialoglycoprotein receptor (ASGP-R) could be assembled on a solid support. This methodol. allowed easy introduction of spaceres, the length of which could be readily accommodated for optimal binding to the ASGP-R.

Tetrahedron published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C19H17N2NaO4S, Related Products of esters-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Medina, Scott H. published the artcileTargeting Hepatic Cancer Cells with PEGylated Dendrimers Displaying N-Acetylgalactosamine and SP94 Peptide Ligands, Recommanded Product: (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, the publication is Advanced Healthcare Materials (2013), 2(10), 1337-1350, database is CAplus and MEDLINE.

Poly(amidoamine) (PAMAM) dendrimers are branched water-soluble polymers defined by consecutive generation numbers (Gn) indicating a parallel increase in size, mol. weight, and number of surface groups available for conjugation of bioactive agents. In this article, we compare the biodistribution of N-acetylgalactosamine (NAcGal)-targeted [¹⁴C]₁-G5-(NH₂)₅-(Ac)₁₀₈-(NAcGal)₁₄ particles to non-targeted [¹⁴C]₁-G5-(NH₂)₁₂₇ and PEGylated [¹⁴C]₁-G5-(NH₂)₄₄-(Ac)₇₃-(PEG)₁₀ particles in a mouse hepatic cancer model. Results show that both NAcGal-targeted and non-targeted particles are rapidly cleared from the systemic circulation with high distribution to the liver. However, NAcGal-targeted particles exhibited 2.5-fold higher accumulation in tumor tissue compared to non-targeted ones. In comparison, PEGylated particles showed a 16-fold increase in plasma residence time and a 5-fold reduction in liver accumulation. These results motivated us to engineer new PEGylated G5 particles with PEG chains anchored to the G5 surface via acid-labile cis-aconityl linkages where the free PEG tips are functionalized with NAcGal or SP94 peptide to investigate their potential as targeting ligands for hepatic cancer cells as a function of sugar conformation (α vs. β), ligand concentration (100-4000 nM), and incubation time (2 and 24 h) compared to fluorescently (Fl)-labeled and non-targeted G5-(Fl)₆-(NH₂)₁₂₂ and G5-(Fl)₆-(Ac)₁₀₇-(cPEG)₁₅ particles. Results show G5-(Fl)₆-(Ac)₁₀₇-(cPEG[NAcGal_β])₁₄ particles achieve faster uptake and higher intracellular concentrations in HepG2 cancer cells compared to other G5 particles while escaping the non-specific adsorption of serum protein and phagocytosis by Kupffer cells, which make these particles the ideal carrier for selective drug delivery into hepatic cancer cells.

Advanced Healthcare Materials published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Recommanded Product: (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics

Hasegawa, Akira published the artcileStudies on the thioglycosides of N-acetylneuraminic acid. 10. Synthesis of s-(α-sialosyl)-(2â†?)-O-2-acetamido-2-deoxy-β-D-hexopyranosyl ceramide and its related compounds, Synthetic Route of 10378-06-0, the publication is Journal of Carbohydrate Chemistry (1992), 11(3), 319-31, database is CAplus.

Title sialosylglycolipid I was prepared via coupling of the sodium salt of α-2-thio-Neu5Ac with 2-azidoethyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-tosyl-β-D-glucoside and condensation with 2-tetradecylhexadecanoic and octadecanoic acids.

Journal of Carbohydrate Chemistry published new progress about 10378-06-0. 10378-06-0 belongs to esters-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Ester,Inhibitor,Inhibitor, name is (3aR,5R,6R,7R,7aR)-5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]oxazole-6,7-diyl diacetate, and the molecular formula is C14H19NO8, Synthetic Route of 10378-06-0.

Referemce:
https://en.wikipedia.org/wiki/Ester,
Ester – an overview | ScienceDirect Topics