117177-19-2

Upstream product

• 7512-17-6 N-Acetyl-D-glucosamine 
• 67-64-1 acetone 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 

Downstream Products

• 1856-93-5 (R)-2-(((3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanoic acid 
• 147126-58-7 octyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 54400-75-8 allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 19124-40-4 isopropyl 2-acetamido-2-deoxy-α-D-glucopyranoside 
• 78341-33-0 isopropyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 1096035-40-3 C₁₄H₂₁NO₇ 
• 17429-94-6 1,4,6-tri-O-acetyl-2-acetamido-2-deoxy-3-methoxy-β-Dglucopyranoside 
• 1349064-53-4 2-azidoethyl 2-acetamido-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 1349065-00-4 2-azidoethyl 2-acetamido-3-O-allyl-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 153373-84-3 methyl 2-acetamido-2-deoxy-β-D-glucofuranosidurono-6,3-lactone 
• 919474-81-0 N-((3S,4R,5R,6R)-1-benzhydryl-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl)acetamide 
• 153373-85-4 methyl (methyl 2-acetamido-2-deoxy-β-D-glucofuranosid)uronate 
• 153373-82-1 methyl 2-acetamido-2-deoxy-β-D-xylo-hexofuranosid-5-ulose 
• 153373-83-2 N-((1R,2R,3S)-1-Formyl-2,3,5-trihydroxy-4-oxo-pentyl)-acetamide 

Relevant academic research and scientific papers

Facile synthesis of d-lividosamine

A simple, four-step synthesis of d-lividosamine starting from N-acetyl-d-glucosamine via a furanosyl oxazoline intermediate is described.

Synthesis of 2-acetamido-1,2,4-trideoxy-1,4-imino-D-galactitol, a new hexosaminidase inhibitor

2-Acetamido-1,2,4-trideoxy-1,4-imino-D-galactitol was synthesised from 2-acetamido-2-deoxy-D-glucose in 12 steps and was shown to be a modest hexosaminidase inhibitor.

Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization

A series of novel 1,3-difunctionalized glycoconjugates were synthesized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 functionalization of sugar molecules was achieved by chemical functionalization of isopropylidene or oxazoline protected sugar derivatives.The structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation.The oxazoline protected D-GlcNAc derivative gave either pyranose or furanose derivatives on glycosidation depending on the amount of Lewis acid used.The diversely functionalized glycoconjugates with azide or alkyne groups are potentially useful for the synthesis of multifunctionalized complex glycoconjugates via click reactions.

Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers

A general and practical route to carbohydrate-aryl ethers by nucleophilic aromatic substitution (SNAr) is reported. Upon treatment with KHMDS, C-O bond formation occurs between carbohydrate alcohols and a diverse range of fluorinated (hetero)ar

Synthesis of N -acetyl glucosamine analogs as inhibitors for hyaluronan biosynthesis

Elevated hyaluronan expression is a hallmark of many types of cancer. Therefore, inhibition of hyaluronan biosynthesis can potentially slow the growth of tumor cells. Herein, we explore a chain termination strategy to reduce hyaluronan synthesis by tumor cells. Several analogs of glucosamine were prepared, which contained modifications at the C-3 positions. These analogs can possibly cap the nonreducing end of a growing hyaluronan chain, thus lowering the amount of hyaluronan synthesized. Upon incubation with pancreatic cancer cells, a fluorine-containing glucosamine analog was found to exhibit significant inhibitory activities of hyaluronan synthesis. Furthermore, it drastically reduced the proliferation of cancer cells. Supplemental materials are available for this article. Go to the publisher's online edition of Journal of Carbohydrate Chemistry to view the supplemental file.

Novel O-acetylated decasaccharides

The present invention relates to diversely acetylated decasaccharides of formula (I) representative of two repeating units of Shigella flexneri serotype 2a O-antigen, conjugates and method of preparation thereof. These compounds exhibit antigenic properties and are particularly useful for the diagnosis of Shigella infection. wherein R1 and R2 are as defined in claim 1.

Regioselective glycosylation of glucosamine and galactosamine derivates using O-pivaloyl galactosyl donors

Penta-O-pivaloyl-galactopyranose and tetra-O-pivaloyl-galactopyranosyl bromide after electrophilic activation reacted with 6-O-protected 2-azido-galactosides to give the precursor structures of the Thomsen-Friedenreich antigen disaccharide with high regioselectivity, but low yield. With 4,6-O-benzylidene protected 2-azidogalactosides and 2-O-pivaloyl phenylthio galactosides, T-antigen disaccharides of this type were obtained in good yields. Glycosylation reactions of 4,6-O-benzylidene protected glucosamine derivatives with O-pivaloyl protected galactosyl bromide efficiently gave lactolactosamine disaccharides. Even a thioglycoside was efficiently galactosylated by this method resulting in the formation of a disaccharide thioglycoside useful itself as a potential glycosyl donor.

Synthesis of 2-acetamido-1,2,4-trideoxy-1,4-imino-D-galactitol and -D-glucitol for evaluation as glycosidase inhibitors

The title compounds, galacto-1 and gluco-2, were synthesised from N-acetyl-D-glucosamine via a common 1,4-diol intermediate that underwent transformations involving either a single or double inversion of stereochemistry at C-4, respectively. In the double

2-Acetamido-1,2-dideoxynojirimycin: An improved synthesis

The potent β-N-acetylglucosaminidase inhibitor, 2-acetamido-1,2-dideoxynojirimycin, was prepared in 6 steps from N-acetyl-D-glucosamine (overall yield 10%) via the double reductive amination of a keto aldehyde as the key step.