177897-27-7

Upstream product

• 117192-23-1 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-C--α-D-xylofuranose 
• 103597-18-8 methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-α-D-glycero-D-gluco-octopyranoside 
• 103597-19-9 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-D-glycero-α-D-glucooct-7-eno-1,5-pyranoside 

Downstream Products

• 103597-21-3 methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside 
• 103597-25-7 methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-gluco-heptopyranoside 
• 103597-24-6 methyl 2,3,4-tri-O-benzyl-L-glycero-α-D-gluco-heptopyranoside 
• 103597-32-6 (R)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-2-trityloxy-ethanol 
• 103597-32-6 (S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-2-trityloxy-ethanol 
• 103597-31-5 Benzoic acid (S)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-2-trityloxy-ethyl ester 
• 103597-26-8 Methanesulfonic acid (R)-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-2-trityloxy-ethyl ester 
• 103597-29-1 (2R,3R,4S,5R,6S)-2-((S)-1-Azido-2-trityloxy-ethyl)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 
• 103597-28-0 Acetic acid (R)-2-methanesulfonyloxy-2-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester 
• 103597-30-4 Acetic acid (S)-2-azido-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester 
• 103597-27-9 Methanesulfonic acid (R)-2-hydroxy-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester 
• 177897-24-4 (E)-(R)-4-Acetoxy-4-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-2-enoic acid methyl ester 
• 888487-37-4 methyl 6-O-acetyl-2,3,4-tri-O-benzyl-7-O-TBDMS-6-D-glycero-α-D-heptoglucopyranoside 
• 177897-23-3 Acetic acid (S)-2-oxo-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl ester 

Relevant academic research and scientific papers

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).

Synthesis of Methyl 2,3,4-tri-O-benzyl-D- and L-glycero-α-D-glucoheptopyranosides

Title compounds 8 and 17 have been synthesized from methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-D- and L-glycero-α-D-gluco-oct-7-ynopyranosides (6 and 15 respectively) in three steps: hydrogenation of the triple bond, ozonolytic cleavage of the resulting double