4271-28-7

Basic information

• Product Name: N-ACETYL-D-GLUCOSAMINITOL
• Synonyms: N-ACETYL-D-GLUCOSAMINITOL;N-acetylglucosaminitol;2-Acetamido-2-deoxy-D-glucitol;N-[(2S,3R,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-yl]acetamide
• CAS NO: 4271-28-7
• Molecular Formula: C₈H₁₇NO₆
• Molecular Weight: 223.223
• Mol File: 4271-28-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 656.5 °C at 760 mmHg
• Flash Point: 350.8 °C
• Appearance: /
• Density: 1.434 g/cm³
• Vapor Pressure: 5.08E-20mmHg at 25°C
• CAS DataBase Reference: N-ACETYL-D-GLUCOSAMINITOL(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYL-D-GLUCOSAMINITOL(4271-28-7)
• EPA Substance Registry System: N-ACETYL-D-GLUCOSAMINITOL(4271-28-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 4271-28-7(Hazardous Substances Data)

Usage

Definition

ChEBI: A 2-deoxyhexitol derivative that is D-glucitol in which the 2-hydroxy substituent is replaced by an acetamido group.

InChI:InChI=1/3C8H17NO6/c3*1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h3*5-8,10-11,13-15H,2-3H2,1H3,(H,9,12)/t3*5-,6+,7+,8+/m000/s1

Upstream product

• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 56211-19-9 2-acetamido-2-deoxy-D-glucitol pentaacetate 
• 2914-23-0 barium methoxide 
• 7732-18-5 water 
• 14131-68-1 N-acetyl-D-glucosamine 
• 1398-61-4 chitin 
• 83050-24-2 N-Benzyl-N-[(1S,2R)-2-benzyloxy-1-benzyloxymethyl-2-((4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-ethyl]-acetamide 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 108-24-7 acetic anhydride 
• 92379-95-8 2-Amino-3-O-methyl-2-desoxy-D-glucose Hydrochlorid 
• 10036-64-3 N-acetyl-D-glucosamine 

Downstream Products

• 74034-09-6 2-acetamido-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-glucitol 
• 53756-28-8 3,6-anhydro-ADS 
• 14307-03-0 2-amino-2-deoxy-D-glucitol 
• 87924-45-6 2-acetamido-3,4,5,6-tetra-O-acetyl-2-deoxy-D-glucose N,N'-diphenylformazan 
• 87924-40-1 2-acetamido-2-deoxy-D-glucose N,N'-diphenylformazan 
• 87924-49-0 2-acetamido-2-deoxy-3,4;5,6-di-O-isopropylidene-D-glucose N,N'-diphenylformazan 
• 87924-37-6 2-acetamido-2-deoxy-D-glucose phenylhydrazone 

Relevant articles and documents

DEAMINATION OF 2-AMINO-2-DEOXYHEXITOLS AND OF THEIR PER-O-METHYLATED DERIVATIVES WITH NITROUS ACID

The products of nitrous acid deamination of per-O-methylated 2-amino-2-deoxy-D-glucitol and of 2-amino-2-deoxy-3-O-β-D-galactopyranosyl-D-glucitol and its per-O-methylated derivative have been characterized by g.l.c.-mass spectrometry after treatment with sodium borodeuteride and further substitution by acetylation, methylation, or (trideuteriomethyl)ation.The results confirm that the most important reaction pathway (1) involves a 12-hydride shift, to give 2-deoxy-D-arabino-hexoses, but that significant side-reactions include (2) solvolytic displacement at C-2, (3) a 32-hydride shift to give 2-deoxy-2-D-erythro-3-hexuloses, and (4) a C-4C-2 migration to give 2-deoxy-2-C-(hydroxymethyl)-D-ribose and -D-arabinose.Reactions (3) and (4) result in elimination of the original 3-O-substituents, with the exposure of new reducing groups, from oligosaccharides terminated by 3-O-substituted 2-amino-deoxyhexitols.

Hydrolytic hydrogenation of chitin to amino sugar alcohol

Chitin is the second most abundant biomass and characteristically contains nitrogen atoms in its monomer units. These favourable features promote chitin to be a potential resource for renewable organonitrogen compounds. 2-Acetamido-2-deoxysorbitol (ADS) is an attractive target in the derivatives of chitin, but the conversion of chitin to ADS has not been reported so far. In this work, we demonstrate the catalytic conversion of chitin to ADS using mechanocatalysis in the presence of H2SO4 and subsequent hydrolytic hydrogenation by H2SO4 and Ru/TiO2 without any purification process. Our study clarified that the yield of ADS is strongly influenced by the reaction temperature and pH. The hydrolysis favourably proceeds at high temperature and low pH (2.0), but the hydrogenation needs a low temperature and a specific pH of 3-4 to achieve high selectivity. Specifically, in the hydrogenation step, an acid causes various side-reactions of amide and hemiacetal groups especially in the presence of a Ru catalyst, whereas even a small amount of base drastically accelerates the retro-aldol reaction to form erythritol and N-acetylethanolamine. Therefore, a one-pot but two-step reaction is necessary to optimise both the hydrolysis and hydrogenation steps and maximise the overall yield of ADS up to 52%.

Preliminary communication. The reaction of O-protected glycosides of 2-benzamido-2-deoxy-β-D-glucose with trimethylsilyl chloride-sodium hydride and subsequent reduction with lithium aluminium hydride

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