205502-41-6

Upstream product

• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 205502-40-5 (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(1-ethoxy-ethoxy)-tetrahydro-pyran-2-ol 
• 158923-64-9 1-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranose 
• 1011723-04-8 glucal epoxide 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 100-44-7 benzyl chloride 
• 65827-55-6 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 205502-42-7 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-isopropenyl-tetrahydro-pyran-3-ol 
• 912650-36-3 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-galacto-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 912650-39-6 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-manno-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 
• 912650-33-0 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulosyl-(2->2)-3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 

Relevant academic research and scientific papers

Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely α-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by 3JC,H coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective.

Oxoammonium salts. Part 8: Oxidations in base: Oxidation of O-1 unprotected monosaccharides to lactones using 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate

The oxidant, 4-acetylamino-2,2,6,6-tetramethylpiperidine-oxoammonium tetrafluoroborate in pyridine/CH2Cl2, is reported to be an excellent reagent for the conversion of hemiacetals to lactones. Specifically, the conversion of 1-O unprotected sugars to their corresponding aldonolactones is achieved in high yields. The basic reaction conditions partially overcome some disadvantages reported for oxoammonium-type oxidants, namely the inability to run the reaction in the presence of acid-labile groups and in the presence of β-oxygens.

Highly stereoselective hydroformylation of olefins possessing chiral sugar templates

Hydroformylation of 1,1-disubstituted olefins possessing chiral sugar templates gave β-substituted aldehydes in good to excellent yields with up to 99% diastereoselectivity.