62867-56-5

Upstream product

• 18422-15-6 2-amino-2-N:3-O-carbonyl-2-deoxy-5,6-isopropylidene-D-glucose diethyl acetal 
• 53958-21-7 4,6-di-O-acetyl-2,3-O-carbonyl-α-D-mannopyranosyl bromide 

Downstream Products

• 34384-80-0 (4R)-4r-diethoxymethyl-5t-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-(tetra-O-acetyl-α-D-mannopyranosyloxy)-methyl]-oxazolidin-2-one 
• 34384-81-1 (4R)-4r-diethoxymethyl-5t-[(S)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-α-D-mannopyranosyloxy-methyl]-oxazolidin-2-one 

Relevant academic research and scientific papers

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.