10375-65-2

Basic information

• Product Name: phenylmethyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-mannopyranoside
• Synonyms: phenylmethyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-mannopyranoside
• CAS NO: 10375-65-2
• Molecular Weight: 437.447
• Mol File: 10375-65-2.mol
• Article Data: 40

Chemical Properties

• CAS DataBase Reference: phenylmethyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenylmethyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-mannopyranoside(10375-65-2)
• EPA Substance Registry System: phenylmethyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-mannopyranoside(10375-65-2)

Safety Data

• Hazardous Substances Data: 10375-65-2(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 62098-31-1 benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside 
• 100-51-6 benzyl alcohol 
• 51533-00-7 2-acetylamino-3,4,6-triacetyl-2-deoxy-α-D-glucopyranosyl bromide 
• 126777-92-2 3,4,6-tetra-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranosyl azide 
• 439-02-1 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl fluoride 
• 134160-64-8 4',5'-epoxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 80035-31-0 benzyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 2873-29-2 D-glucal triacetate 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 126777-99-9 3,4,6-tetra-O-acetyl-2-deoxy-2-iodo-β-D-glucoopyranosyl azide 

Downstream Products

• 109068-32-8 benzyl-(2-acetylamino-tri-O-methyl-2-deoxy-β-D-glucopyranoside) 
• 3055-51-4 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 851189-13-4 benzyl 2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside 
• 79184-08-0 3,4,6-tri-O-acetyl-2-acetamido-1-O-[bis(benzyloxy)phophoryl]-2-deoxy-α-D-glucopyranose 
• 147072-52-4 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphanyloxy)-tetrahydro-pyran-4-yl ester 
• 13343-61-8 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 10375-65-2 benzyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-glucopyranoside 

Relevant articles and documents

New procedure for the preparation of 2-(trimethylsilyl)ethyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside and other alkyl β-glycosides

The title compound and other alkyl β-glycosides 1a-g can be prepared in one step from commercially available 2-acetamido-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose (3) and simple alcohols using camphorsulfonic acid as a promoter together with azeotr

Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs

Lipo-chitotetrasaccharide analogues where one central GlcNAc residue was replaced by a triazole unit have been synthesized from a derivative obtained by chitin depolymerization and a functionalized N-acetyl-glucosamine via the copper-catalyzed azide-alkyn

Synthesis of N-acetylsugar-β-trans-glycosides: Facile one-pot transglycosylation of epoxypentyl tri-0-acetyl-N-acetylglucosamine

Glycosides 10 and 11 were prepared from epoxypentyl β-D-N-acetylglucosamine 8 under mild conditions, using TMS triflate as the promotor. Presumably, this novel reaction proceeds via in situ activation of the intermediate oxazoline 9.

-

-

The effect of deoxyfluorination and: O -acylation on the cytotoxicity of N -acetyl-d-gluco- And d-galactosamine hemiacetals

Fully acetylated deoxyfluorinated hexosamine analogues and non-fluorinated 3,4,6-tri-O-acylated N-acetyl-hexosamine hemiacetals have previously been shown to display moderate anti-proliferative activity. We prepared a set of deoxyfluorinated GlcNAc and GalNAc hemiacetals that comprised both features: O-acylation at the non-anomeric positions with an acetyl, propionyl and butanoyl group, and deoxyfluorination at selected positions. Determination of the in vitro cytotoxicity towards the MDA-MB-231 breast cancer and HEK-293 cell lines showed that deoxyfluorination enhanced cytotoxicity in most analogues. Increasing the ester alkyl chain length had a variable effect on the cytotoxicity of fluoro analogues, which contrasted with non-fluorinated hemiacetals where butanoyl derivatives had always higher cytotoxicity than acetates. Reaction with 2-phenylethanethiol indicated that the recently described S-glyco-modification is an unlikely cause of cytotoxicity.

MONOSACCHARIDE PHOSPHORAMIDATE PRODRUGS

The present disclosure provides monosaccharide phosphoramidate prodrugs of monosaccharide monophosphates. The present disclosure further provides methods of treating diseases of conditions such as congenital disorders of glycosylation comprising administering the monosaccharide phosphoramidate prodrugs of the present disclosure to a patient in need thereof.