125287-99-2

Upstream product

• 125287-96-9 methyl [methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-6(E)-eno-α-D-gluco-oct-1,5-pyranosid]uronate 

Downstream Products

• 115520-86-0 methyl 2,3,4-tri-O-benzyl-D-threo-α-D-gluco-oct-1,5-pyranoside 
• 167083-93-4 {2-[(4S,5R)-2,2-Dimethyl-5-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-[1,3]dioxolan-4-yl]-2-oxo-ethyl}-phosphonic acid dimethyl ester 
• 204707-03-9 (methyl 2,3,4-tri-O-benzyl-6,7-O-isopropylidene-D-threo-α-D-gluco-oct-1,5-pyranosid-8-uronyl)-(triphenylphosphoranylidene)methane 
• 204707-02-8 (4S,5R)-2,2-Dimethyl-5-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-[1,3]dioxolane-4-carboxylic acid 
• 115520-89-3 methyl 2,3,4-tri-O-benzyl-β-L-threo-D-manno-octopyranoside 
• 115520-90-6 methyl 2,3,4-tri-O-benzyl-α-D-threo-D-manno-octopyranoside 

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.

Simple synthesis of D-erythro- and L-erythro-D-gluco-octoses

Synthesis of the previously unknown methyl 2,3,4-tri-O-benzyl-L-erythro-β-D-gluco-and D-erythro-α-D-gluco-oct-1,5-pyranosides (1 and 2) was accomplished on two independent routes via either cis-hydroxylation of stereoisomeric 6-C-vinyl-L-glycero-β-D-gluco

Application of stabilized sugar-derived phosphoranes in the synthesis of higher carbon monosaccharides. First synthesis of a C21-dialdose

C21 Monosaccharide precursors 11 and 12 were synthesized by a coupling of a C12 aldehyde 1 with C9 stabilized phosphoranes 2 and 3 respectively. The 'smaller' C19 sugar 13 was prepared from a C12 alde

Higher-Carbon Sugars. Part 13. The Catalytic Osmylation of Some α,β-Unsaturated Octuronic Acid Derivatives and a Synthesis of (meso)-threo-gluco-Octitol

In compliance with Kishi's empirical rule, catalytic osmylation of methyl uronate (6) produced a mixture of methyl (methyl 2,3,4,-tri-O-benzyl-β-L-threo-D-gluco-octopyranosid)uronate