62867-67-8

Basic information

• Product Name: N-[(2R,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• Synonyms: N-[(2R,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS NO: 62867-67-8
• Molecular Weight: 922.085
• Mol File: 62867-67-8.mol

Chemical Properties

• CAS DataBase Reference: N-[(2R,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(2R,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide(62867-67-8)
• EPA Substance Registry System: N-[(2R,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide(62867-67-8)

Safety Data

• Hazardous Substances Data: 62867-67-8(Hazardous Substances Data)

Downstream Products

• 186765-90-2 2-acetamido-2-deoxy-4-O-(β-D-mannopyranosyl)-β-D-glucosamine 
• 62867-68-9 benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-α-D-glucopyranoside 

Relevant articles and documents

The synthesis of 2-acetamido-2-deoxy-4-O-beta-D-mannopyranosyl-D-glucose.

Condensation of 4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl bromide with 2-amino-2-N,3-O-carbonyl-5.6-O-isopropylidene-D-glucose diethyl acetal gave, unexpectedly, 2-amino-2-N,3-O-carbonyl-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-O-carbonyl-alpha-D-mannopyranosyl)-5,6-O-isopropylidene-D-glucose diethyl acetal, futher transformed, by de-esterification followed by acetylation, into the previously known 2-amino-2-N,3-O-carbonyl-2-deoxy-5,6-O-isopropylidene-4-O-alpha-D-mannopyranosyl-D-glucose diethyl acetal and its tetra-O-acetyl derivative. Benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside was condensed with 2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranosyl bromide to give benzyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-beta-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside. Removal of the 2-O-acetyl group, followed by oxidation with acetic anhydridedimethyl sulfoxide, gave a beta-D-arabino-hexosid-2-ulose (25). After reduction with sodium borohydride, removal of the benzyl groups gave crystalline 2-acetamido-2-deoxy-4-O-beta-D-mannopyranosyl-D-glucose (27). The anomeric configuration of the glycosidic linkage was ascertained by comparison with the alpha-D-linked disaccharide.