Gross, Paul H. et al. published their research in Justus Liebigs Annalen der Chemie in 1966 | CAS: 6730-10-5

Amino sugar synthesis. XVII. Synthesis of D-rhamnosamine and of 2,6-diamino-2,6-dideoxy-D-mannose from N-acetyl-D-mannosamine was written by Gross, Paul H.;Brendel, Klaus;Zimmerman, Howard K. Jr.. And the article was included in Justus Liebigs Annalen der Chemie in 1966.Synthetic Route of C16H23NO10 This article mentions the following:

2-acetamido-2-deoxy-D-mannose-H₂O (I) by 2 distillations under reduced pressure with 500 ml. 1:2 C₆H₆-EtOH azeotrope, then addition of 40 g. Dowex 50WX2 (H⁺ form) resin (similarly dehydrated), distillation with 2.5 l. azeotrope slowly at 760 mm., and working up the EtOH solution and washings gave 15.5 g. sirupy Et 2-acetamido-2-deoxy-D-mannoside (II), giving a neg. Fehling test and consuming 0.9 mole NaIO₄ in 6 hrs. (0.15-0.2 mole HCHO formed). Extracting the resin with 150 ml. 2N HCl 6 times gave 6 g. 2-amino-2-deoxy-D-mannose-HCl (III), [浼猐²³_D -4鎺?(c 0.33, H₂O). 2-Acetamidotetra-O-acetyl-2-deoxy-灏?D-mannose, obtained from I or III with Ac₂O and C₅H₅N, m. 160-1鎺? [浼猐²⁵_D – 19鎺? II (3 g.) and Ph₃CCl in C₅H₅N 2 hrs. at 90鎺?gave 4.6 g. 6-O-trityl ether, m. 160-1鎺? [浼猐²³_D -9鎺?(c 2, C₅H₅N); hydrolysis of the Ph₃C group with aqueous HOAc and NaIO₄ oxidation showed 19% furanoside. II triacetate (from Ac₂O and C₅H₅N 10 hrs. at room temperature) was a sirup, [浼猐²³_D 60鎺?(c 3.6, CHCl₃). Reaction of 10 g. II and 8 g. p-MeC₆H₄SO₂Cl in C₅H₅N 8 days at 0鎺?then addition of 12 ml. Ac₂O and reaction 36 hrs. at 0鎺?gave 34% 6-(O-p-tolylsulfonyl) derivative (IV), m. 135-6鎺? [浼猐²³_D 54鎺?(c 2, C₅H₅N). Heating IV with KOAc, Ac₂O, and AcOH 15 hrs. at 130鎺?gave, not the expected II triacetate, but a half-crystalline substance, which was deacetylated and showed, by NaIO₄ oxidation, a 5% furanoside content. Heating IV and NaI in EtAc 15 hrs. at 110鎺?gave 88% 6-deoxy-6-iodo derivative, m. 56-8鎺? [浼猐²³_D 44鎺?(c 2, C₅H₅N), hydrogenated over Raney Ni 10 hrs., and the product hydrolyzed in 2N HCl 1 hr. at 60鎺? then 2 hrs. at 100鎺? to give 71% 2-amino-2,6-dideoxy-D-mannose-HCl, m. 175鎺?(decomposition), [浼猐²⁵_D -28鎺?(5 min.) to -23鎺?(4 hrs.) (c 0.33, H₂O), [浼猐²⁵₅₄₆ -26鎺?(12 hrs., c 0.33, H₂O). The 6-azido-6-deoxy derivative, prepared from 4.87 g. IV and 5 g. NaN₃ in 25 ml. Me₂SO 3 hrs. at 110鎺? 98% yield, was an oil, which was hydrogenated 5 hrs. over Pd black in MeOH and Ac₂O to give 74% Et 2,6-diacetamido-3,4-di-O-acetyl-2,6-dideoxy-浼?D-mannopyranoside, m. 225-6鎺? [浼猐)²⁴_D 71鎺?(c 2, C₅H₅N), and then hydrolyzed 1 hr. at 60鎺?and 2 hrs. at 100鎺?in 3N HCl to give 72% 2,6-diamino-2,6-dideoxy-浼?D-mannose-2 HCl, m. 135-6鎺?[浼猐²⁴_D 9鎺?(10 min.) to -1鎺?(25 hrs.). Reaction of 50 mg. 2,6-diamino-2,6-dideoxy-浼?D-glucose-2HCl in 1 ml. H₂O, and 5 ml. MeOH with 7 ml. 1% AgOAc and 0.5 ml. Ac₂O 48 hrs. in the dark, treatment with cation-exchange resin, and crystallization from MeCH(OMe)₂ gave 35 mg. 2,6-diacetamido-2,6-dideoxy-浼?D-glucose, m. 208-9鎺?(decomposition), [浼猐²⁰_D 36鎺?(2 hrs.) to 32鎺?(15 hrs., c 0.5, H₂O). In the experiment, the researchers used many compounds, for example, (2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (cas: 6730-10-5Synthetic Route of C16H23NO10).

(2S,3S,4R,5S,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate (cas: 6730-10-5) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.Synthetic Route of C16H23NO10

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics