135284-41-2

Upstream product

• 35958-64-6 (3R,4R)-4-Benzyloxy-5-((R)-1,2-bis-benzyloxy-ethyl)-tetrahydro-furan-2,3-diol 
• 35958-64-6 3,5,6-Tri-O-benzyl-α,β-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 53928-30-6 1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside 
• 35958-64-6 3,5,6-Tri-O-benzyl-D-glucofuranose 

Downstream Products

• 135284-50-3 Imidazole-1-carbothioic acid O-{(1R,2R)-2,3-bis-benzyloxy-1-[(R)-benzyloxy-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-propyl} ester 
• 135284-44-5 (2S,3S,5S)-3,5,6-Tris-O-benzyl-1,2-O-isopropylidene-1,2,3,5,6-hexane-pentol 
• 58846-24-5 3,4,5,6-tetra-O-benzyl-D-sorbitol 
• 58794-70-0 1,2-O-isopropylidene-3,4,5,6-tetra-O-benzyl-D-sorbitol 
• 903876-35-7 3,5,6-tri-O-benzyl-4-O-tosyl-D-glucitol 
• 903876-34-6 3,5,6-tri-O-benzyl-1,2-O-isopropylidene-4-O-tosyl-D-glucitol 
• 903876-38-0 1,4-anhydro-3,5,6-tri-O-benzyl-D-tagatose diethyl acetal 
• 871508-19-9 1,4-anhydro-3,5,6-tri-O-benzyl-D-fructose diethyl acetal 
• 903876-36-8 1,4-anhydro-3,5,6-tri-O-benzyl-D-galactitol 
• 903876-37-9 1,4-anhydro-3,5,6-tri-O-benzyl-D-tagatose 
• 871508-18-8 1,4-anhydro-3,5,6-tri-O-benzyl-D-fructose 
• 135284-42-3 (2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol 
• 903876-33-5 1,4-anhydro-3,5,6-tri-O-benzyl-D-glucitol 
• 135310-56-4 [(4S,5R,6R)-5-Benzyloxy-6-((R)-1,2-bis-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-methanol 

Relevant academic research and scientific papers

Synthesis of 1,4-anhydro-d-fructose and 1,4-anhydro-d-tagatose

1,4-Anhydro-d-fructose and 1,4-anhydro-d-tagatose were prepared from 1,2-O-isopropylidene-d-glucofuranose via the common intermediate 3,5,6-tri-O-benzyl-d-glucitol. The title compounds may be interesting anti-oxidants and feature activities akin to their natural pyranoid counterpart, 1,5-anhydro-d-fructose.

Preparation of sugar-derived α-acetoxy-aldehydes

A convenient method for conversion of sugar diols (2a-2d) into a-acetoxy-aldehydes: 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranos-6-ulose (5a), 5-O-acetyl-3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranos-6-ulose (5b), methyl 6-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco- and L-glycero-α-D-gluco-heptopyranosid-7-uloses (5c and 5d respectively) is presented. This involves the protection (as TBDMS ether) of the primary hydroxyl group, acetylation of the remaining secondary one and desilylation followed by a Swern oxidation. Partial migration of the acetyl group during desilylation (with Bu4NF) was observed for compound 4a and complete migration for 4f. α-Acetoxy-aldehydes 5a-5d were characterized as adducts with Ph3P = CH-CO2Me (12a-12d).

Enantiospecific Synthesis of (2S,3S,5S)-2-Acetamido-2,4-dideoxyhexopyranose (N-Acetyl-4-deoxy-D-mannosamine) from D-Glucose

A 14-step enantiospecific total synthesis (overall yield 6percent) of the title compound 1 from the known furanose 4 (derived from D-glucose) is described. Key Words: Carbohydrates, total synthesis of / Amino sugars / Mannosamine