297747-92-3

Upstream product

• 389885-51-2 C₆₁H₅₆N₂O₁₇ 
• 175289-51-7 2,3,3',4,4'-penta-O-benzyl-6,6'-di-p-nitrobenzoylsucrose 
• 297747-84-3 methyl (2,3,4-tri-O-benzyl-6-O-p-nitrobenzoyl-α-D-glucopyranosyl)-(1<->4)-[(E)-5,6-di-O-benzyl-2,3-dideoxy-8-O-p-nitrobenzoyl-β-D-arabino-oct-2-eno-4-ulofuranosid]onate 

Relevant academic research and scientific papers

Synthesis and structural analysis of higher analogs of sucrose

Three sucrose monoalcohols with free hydroxyl groups at C-1', C-6, and C-6' (1, 4, and 6) were prepared selectively and in good yield from 2,3,3',4,4'-penta-O-benzylsucrose. These compounds were oxidized to aldehydes and reacted with stabilized ylide, Ph3P=CHCO2Me to afford appropriate α,β-unsaturated esters 10, 11, and 12. Each olefin was cis-hydroxylated with OsO4/NMO to stereoisomeric diols 13/14, 15/16, and 17/18, configurations of which were assigned by chemical correlation and CD evaluation. Stereoselectivity of the osmylation reaction was surprisingly low (ca 3:2), especially as compared to a similar process performed on simple derivatives of 6,7-unsaturated methyl glycosides for which the ratio of isomeric diols was assigned as 10:1. The osmylation of 11 (derivative homologated by a C2-unit at the glucose part) did not obey Kishi's rule. Horner-Emmons reaction of sucrose aldehyde 7 with a sugar-derived phosphonate 22 afforded α,β-unsaturated derivative 24, homologated by a C7-unit at the glucose end.