136305-59-4

Upstream product

• 127994-68-7 methyl onate 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 404377-25-9 methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal 
• 110390-66-4 methyl (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-5,6-dihydro-4H-pyran-2-carboxylate 

Downstream Products

• 136305-60-7 methyl 4,5,7-tri-O-benzyl-3-O-t-butyldimethylsilyl-α-D-gluco-hept-2-ulopyranosonate 
• 404377-35-1 methyl 3-O-acetyl-4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate 
• 136305-65-2 (3aS,5R,6R,7S,7aR)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-3a-carboxylic acid 
• 55628-55-2 1,2-O-isopropylidene-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 137500-98-2 methyl 4,5,7-tri-O-benzyl-3-O-t-butyldimethylsilyl-2-deoxy-2-fluoro-α/β-D-gluco-hept-2-ulopyranosonate 
• 136305-49-2 (3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-tetrahydro-pyran-2-carboxylic acid 
• 136305-51-6 methyl (methyl 4,5,7-tri-O-benzyl-3-O-t-butyldimethylsilyl-α/β-D-gluco-hept-2-ulopyranosid)onate 
• 136305-50-5 methyl 4,5,7-tri-O-benzyl-3-O-t-butyldimethylsilyl-2-chloro-2-deoxy-α/β-D-gluco-hept-2-ulopyranosonate 
• 136305-66-3 methyl 3,4,6-tri-O-benzyl-2-O-t-butyldimethylsilyl-β-D-glucopyranoside 
• 40246-30-8 methyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 404377-30-6 methyl 2,4,5,7-tetra-O-benzyl-3-O-thiobenzoyl-α-D-gluco-2-heptulopyranosonate 
• 404377-28-2 methyl 2,4,5,7-tetra-O-benzyl-α-D-gluco-2-heptulopyranosonate 
• 404377-32-8 methyl 2,4,5,7-tetra-O-benzyl-3-deoxy-α-D-arabino-2-heptulopyranosonate 
• 136305-64-1 methyl 4,5,7-tri-O-benzyl-2,3-O-isopropylidene-α-D-gluco-hept-2-ulopyranosonate 

Relevant academic research and scientific papers

Efficient synthesis of 3-deoxy-D-arabino-2-heptulosonate (DAH) and -D-gluco-2-heptulosonate by a two-carbon chain elongation of D-arabinose

Reaction of α-lithiated methyl glyoxylate diethyl mercaptal (3) with 2,3,5-tri-O-benzyl-D-arabinose (2) stereoselectively afforded the D-gluco-2-heptulosonate derivative 4. Mercaptal cleavage led to the corresponding pyranose 5a which could be directly transformed into unprotected D-gluco-2-heptulosonic acid (1a), one of the target molecules. Deoxygenation of 5a at C-3 could also be readily accomplished as its 3-hydroxy group is unprotected. Thus, the second target molecule, 1b, was obtained in just a few steps.

Diastereoselective Free-Radical Reactions. Part 3. The Methyl Glucopyranos-1-yl and 1,2-O-Isopropylideneglucopyranos-1-yl Radicals: Conformational Effects on Diastereoselectivity

The 3,4,6-tri-O-benzyl-2-O-t-butyldimethylsilyl-1-O-methyl-D-glucopyranos-1-yl and the 3,4,6-tri-O-benzyl-1,2-O-isopropylidene-D-glucopyranos-1-yl radicals are quenched with high selectivity (>25:1) from the α- and β-face, respectively, by t-dodecanethiol

Diastereoselective radical reactions : β-face selective quenching of the 1,2-O-isopropylidene-3,4,6-tri-O-benzyl-D-glucopyranos-1-yl radical

Pyrolysis of 3,4,6-tri-Obenzyl-1-carbomethoxy-1,2-dideoxy-1-phenylsulfonyl-D-glucopyranose provides the corresponding 1-carbomethoxyglucal which reacts with osmium tetroxide to form a gluco-diol. This diol is converted to an acetonide which is saponified