Category: 106391-88-2

Asano, Akiko published the artcileAscidiacyclamides containing oxazoline and thiazole motifs assume square conformations and show high cytotoxicity, Recommanded Product: (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, the publication is Journal of Peptide Science (2018), 24(10), n/a, database is CAplus and MEDLINE.

Four cyclic octapeptides were designed from ascidiacyclamide [cyclo(-Ile-Oxz-D-Val- Thz-)₂] (ASC, 1) to investigate the effects of oxazoline (Oxz) and thiazole (Thz) rings on the structures and cytotoxicities of the peptides. Cyclo(-Ile-Thz-D-Val-Oxz-)₂ (2) had the same number of Oxz and Thz rings as ASC, but the ring positions were switched. Cyclo(-Ile-Oxz-D-Val-Thz-Ile-Thz-D-Val-Thz-) (3) and cyclo(-Ile-Thz-D-Val-Oxz-Ile-Thz-D-Val-Thz-) (4) contained one Oxz and three Thz rings within the mol. All Oxz rings were substituted with Thz in cyclo(-Ile-Thz-D-Val-Thz-)₂ (5). These analogs had new Oxz and Thz blocks forming the 24-membered ring. Based on CD spectra and X-ray diffraction analyses, the structures of all four analogs were classified as square ASC forms. But the structures of 2 and 5 differed from the original square form of 1, and they showed no cytotoxicity. The structure of 3 was very similar to that of 1, and 3 showed 10 times greater cytotoxicity than 1. Although no definite structure of 4 was obtained, it showed three times greater cytotoxicity than 1. It appears that the position and number of Oxz residues are essential determinants in the structure-cytotoxicity relationship of ASC analogs.

Journal of Peptide Science published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Recommanded Product: (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate.

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

Takizawa, Toshiya published the artcileTotal synthesis of spiruchostatin A, a potent histone deacetylase inhibitor, Related Products of esters-buliding-blocks, the publication is Heterocycles (2008), 76(1), 275-290, database is CAplus.

Total synthesis of spiruchostatin A, a potent histone deacetylase inhibitor, was achieved. The method features (i) Julia-Kocienski olefination of a tetrazolyl sulfone with an appropriate aldehyde to install the requisite (E)-olefin unit, (ii) amide coupling to produce the key seco-acid, and (iii) subsequent macrolactonization employing Shiina reagent to efficiently construct the desired 15-membered macrocycle.

Heterocycles published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C6H12O2, Related Products of esters-buliding-blocks.

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

Nakano, Ayako published the artcileβ-Isocupreidine-Catalyzed Baylis-Hillman Reaction of Chiral N-Boc-α-Amino Aldehydes, Product Details of C10H19NO3, the publication is Organic Letters (2006), 8(23), 5357-5360, database is CAplus and MEDLINE.

β-Isocupreidine (β-ICD)-catalyzed Baylis-Hillman reaction of chiral N-Boc-α-amino aldehydes BocNR¹CHR²CHO [Boc = Me₃CO₂C; R¹ = H, R² = Me, Me₂CH, Me₂CHCH₂; R¹R² = (CH₂)₃, CMe₂OCH₂] and 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) takes place without racemization and exhibits the match-mismatch relationship between the substrate and the catalyst. In the case of acyclic amino aldehydes, L-substrates show excellent syn selectivity and high reactivity in contrast to D-substrates. On the other hand, in the case of cyclic amino aldehydes, D-substrates rather than L-substrates show excellent anti selectivity and high reactivity. The Baylis-Hillman adducts obtained were transesterified and further converted into carboxyvinyl-substituted oxazolidines and (hydroxy)(methylene)pyrrolidinones.

Organic Letters published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Product Details of C10H19NO3.

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

Cytlak, Tomasz published the artcileFunctionalization of α-hydroxyphosphonates as a convenient route to N-tosyl-α-aminophosphonates, Product Details of C10H19NO3, the publication is RSC Advances (2018), 8(22), 11957-11974, database is CAplus and MEDLINE.

Direct conversion of the α-hydroxyl group by para-toluenesulfonamide to yield α-(N-tosyl)aminophosphonates is reported. α-Aminophosphonates 23a,b–37a,b were obtained from the corresponding α-hydroxyphosphonates 6a,b–21a,b in the presence of K₂CO₃, via the retro-Abramov reaction of the appropriate aldehydes, 1–5. The subsequent formation of imines with simultaneous addition of di-Et phosphite provided access to the α-sulfonamide phosphonates 23a,b–37a,b with better diastereoselectivity than in the case of the Pudovik reaction. The mechanism for this transformation is proposed herein. When Cbz N-protected aziridine 9a,b and phenylalanine analog 12a,b were exploited, intramol. substitution was observed, leading to the corresponding epoxide 38 as the sole product, or oxazolidin-2-one 39 as a minor product. Analogous substitution was not observed in the case of proline 18a,b and serine 21a,b derivatives

RSC Advances published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Product Details of C10H19NO3.

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

Fehrentz, Jean-Alain published the artcileSynthesis of chiral N-protected α-amino aldehydes by reduction of N-protected N-carboxyanhydrides (UNCAs), Name: (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, the publication is Tetrahedron Letters (1994), 35(48), 9031-4, database is CAplus.

Pure N-protected (Boc, Z, Fmoc) α-amino aldehydes were obtained in high yields by reduction of N-protected N-carboxyanhydrides with equivalent amounts of LiAlH(OCMe₃)₃ or lithium tris[(3-ethyl-3-pentyl)oxy]aluminum hydride (LTEPA) in THF as solvent. The reaction is simple, rapid and proceeds without detectable racemization.

Tetrahedron Letters published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Name: (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate.

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

Asano, Akiko published the artcileConformational properties of ascydiacyclamide analogs with cyclic α-amino acids instead of oxazoline residues, SDS of cas: 106391-88-2, the publication is Bioorganic & Medicinal Chemistry (2017), 25(24), 6554-6562, database is CAplus and MEDLINE.

Ascidiacyclamide [ASC, cyclo(-Ile-oxazoline-D-Val-thiazole-)₂] is a cyclic octapeptide isolated from tunicates. We designed ASC analogs [cyclo(-Ile-Xxx-D-Val-thiazole-)₂] in which Pro or a homolog was substituted for oxazoline: [Pro]ASC (Xxx: proline), [Aze]ASC (Xxx: (S)-Azetidine-2-carboxylic acid), [Pip]ASC (Xxx: (S)-Piperidine-2-carboxylic acid) and [ΔPro]ASC (Xxx: (S)-3-pyrroline-2-carboxylic acid) to explore their potential to serve as substitutes for the oxazoline ring. The conformations of these analogs were examined using X-ray diffraction, ¹H NMR and CD spectroscopy. In both the crystal and solution states, the conformations of [Pro]ASC, [Aze]ASC and [ΔPro]ASC were novel square structures having two trans imide bonds and stabilized by two intramol. hydrogen bonds. The crystal structure of [Pip]ASC was a folded conformation with cis and trans imide bonds. Three isomers (cc, ct and tt) were present in a solution of [Pip]ASC. From crystal structures, the degree of puckering in the side chains of Pro and its homologues was estimated to be in the order Pip > Pro > Aze > ΔPro. [Pro]ASC and [Pip]ASC showed strong cytotoxicity, but [Aze]ASC and [ΔPro]ASC showed no cytotoxicity. Among the four analogs, there is consistency between the prolyl ring puckering and cytotoxicity, but not between the peptide backbone structure and cytotoxicity.

Bioorganic & Medicinal Chemistry published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, SDS of cas: 106391-88-2.

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

Kawano, Tomikazu published the artcileSynthesis, reaction, and structure of chiral N-methyl-2-oxazolidinones from 3-ethoxy-6-(N-methyl-N-tert-butoxycarbonyl)amino-2,4-hexadienoates, Application of (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, the publication is Tetrahedron Letters (1997), 38(47), 8219-8222, database is CAplus.

N-methyl-2-oxazolidines I [(S)-CH₂Ph, (R)-CH₂Ph, (S)-CHMe₂, (R)-CHMe₂, H] and their enol Et ethers are obtained stereo- and regioselectively when Me₃CO₂CNMeCHRCH:CHC(OEt):CHCO₂Et are treated with concentrated sulfuric acid (1.0 equivalent) supported on silica gel in dichloromethane at 0° C.

Tetrahedron Letters published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Application of (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate.

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

Kawano, Tomikazu published the artcileSynthesis and reaction of chiral 4,5-disubstituted 2-oxazolidinones from 3-ethoxy-6-[alkyl(tert-butoxycarbonyl)amino]hexa-2,4-dienoates in the presence of concentrated sulfuric acid supported on silica gel, Related Products of esters-buliding-blocks, the publication is Heterocycles (2000), 52(3), 1261-1278, database is CAplus.

Reaction of chiral 3-ethoxy-6-[alkyl(tert-butoxycarbonyl)amino]hexa-2,4-dienoates and related compounds with 97% concentrated sulfuric acid supported on silica gel proceeded stereo- and regioselectively to yield chiral 4,5-disubstituted N-alkyl-2-oxazolidinones. The oxazolidinones were converted to N-alkyl-2-pyrrolylacetates and 2-oxazolidinone derivatives, which can serve as a chiral auxiliary.

Heterocycles published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Related Products of esters-buliding-blocks.

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

Takizawa, Toshiya published the artcileSynthetic studies on spiruchostatin A, a potent histone deacetylase inhibitor, Quality Control of 106391-88-2, the publication is Journal of Tohoku Pharmaceutical University (2007), 33-47, database is CAplus.

Spiruchostatin A (I), isolated from a culture broth of Pseudomonas sp., has been shown to be a potent histone deacetylase (HDAC) inhibitor. HDAC inhibitors can suppress the growth of human tumor xenografts, this natural product, therefore, is expected to be a promising candidate for novel mol.-targeted anticancer agents. We envisioned that I would be synthesized through twofold macrolactam/macrolactone cyclization of a fully elaborated acyclic disulfide. The key segments, required for the preparation of the advanced key intermediate, were initially synthesized, and the two segments were subsequently subjected to the critical cross S-S coupling reaction to produce a desired key intermediate. Upon deprotection of the N-Boc and the Me ester groups, the crucial cyclization formation was achieved using PyBOP to provide a desired macrolactam, a potential key precursor for I. Further investigations concerning the transformation of 16 to the target mol. I were also described.

Journal of Tohoku Pharmaceutical University published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C8H11NO, Quality Control of 106391-88-2.

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

Sayar, Noel published the artcileFacile total synthesis of thailandepsins D-F: Novel bicyclic depsipeptide histone deacetylase inhibitors isolated from a microorganism, Safety of (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, the publication is Synthesis (2019), 51(6), 1419-1426, database is CAplus.

The naturally occurring bicyclic depsipeptide histone deacetylase inhibitors thailandepsins D-F were efficiently synthesized for the first time in 49-61% overall yield over five steps, starting from known amine and carboxylic acid segments. The synthesis includes the condensation of the two known starting materials to directly assemble the corresponding seco-acids, which are the key precursors for macrolactonization. The seco-acids are then macrolactonized using the Shiina method to construct the requisite 15-member macrocycles.

Synthesis published new progress about 106391-88-2. 106391-88-2 belongs to esters-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Aldehyde, name is (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate, and the molecular formula is C10H19NO3, Safety of (R)-tert-Butyl (3-methyl-1-oxobutan-2-yl)carbamate.

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