13343-61-8

Basic information

• Product Name: BENZYL 2-ACETAMIDO-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE
• Synonyms: N-(6-Benzyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide
• CAS NO: 13343-61-8
• Molecular Formula: C₂₂H₂₅NO₆
• Molecular Weight: 399.44
• Product Categories: Carbohydrates & Derivatives
• Mol File: 13343-61-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 241-252°C
• Appearance: /
• Refractive Index: 1.609
• Storage Temp.: -20°C Freezer
• Solubility: DMF (Slightly), Methanol (Slightly, Heated)
• CAS DataBase Reference: BENZYL 2-ACETAMIDO-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 2-ACETAMIDO-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(13343-61-8)
• EPA Substance Registry System: BENZYL 2-ACETAMIDO-4,6-O-BENZYLIDENE-2-DEOXY-BETA-D-GLUCOPYRANOSIDE(13343-61-8)

Safety Data

• Hazardous Substances Data: 13343-61-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C22H25NO6/c1-14(24)23-18-19(25)20-17(13-27-21(29-20)16-10-6-3-7-11-16)28-22(18)26-12-15-8-4-2-5-9-15/h2-11,17-22,25H,12-13H2,1H3,(H,23,24)/t17?,18-,19+,20+,21?,22+/m0/s1

Upstream product

• 3055-51-4 benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 10375-65-2 benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 100-51-6 benzyl alcohol 
• 3055-51-4 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 2873-29-2 D-glucal triacetate 
• 95451-80-2 Benzyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-mannopyranosid 
• 68733-20-0 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside 
• 95451-81-3 Benzyl-2-azido-2-desoxy-α-D-mannoopyranosid 
• 95451-93-7 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide 
• 35812-81-8 Benzyl-2-amino-2-desoxy-α-D-mannopyranosid 
• 25320-99-4 benzyl α-D-glucopyranoside 
• 79549-73-8 benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside 
• 492-62-6 alpha-D-glucopyranose 

Downstream Products

• 95451-85-7 (Benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid)uronsaeure 
• 95451-84-6 benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid 
• 74842-55-0 N-acetyl-1-O-benzyl-4,6-O-benzylidenemuramic acid 
• 13320-00-8 benzyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 13347-83-6 benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside 
• 86781-96-6 benzyl 2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 572909-53-6 benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-glucopyranoside 
• 62867-64-5 benzyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 62867-63-4 benzyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranoside 

Relevant articles and documents

PHOSPHORAMIDATES OF MONOSACCHARIDES

The present invention relates novel phosphorainidates of monosaccharides of formula (I), wherein R1 is a monosaccharide group selected from A and B: R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16 and X are as defined herein. Preferably X is -0-. The present invention also provides processes for the production of compounds of formula (I), pharmaceutical compositions comprising these compounds, as well as to the use thereof in medical therapy, preferably in the treatment of osteoarthritis. Formula (I) wherein: R1 is selected from A and B.

Novel phosphoramidate prodrugs of N-acetyl-(d)-glucosamine with antidegenerative activity on bovine and human cartilage explants

(d)-Glucosamine and other nutritional supplements have emerged as safe alternative therapies for osteoarthritis (OA), a chronic and degenerative articular joint disease. In our preceding paper, a series of novel O-6 phosphate N-acetyl (d)-glucosamine prod

Optimization of UDP-N-acetylmuramic acid synthesis

UDP-N-acetylmuramic acid (UDP-MurNAc) is a substrate of MurC, an important enzyme in the intracellular pathway of bacterial peptidoglycan biosynthesis. Various approaches towards preparation of UDP-Mur/VAc have been published but these synthetic preparations were shown to include many problematic steps. An optimization study with the focus on muramyl phosphate and UMP-morpholidate coupling was performed, resulting in a synthetic procedure enabling robust and easily reproducible production on a multi-gram scale.