77481-70-0

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 67974-18-9 methyl 4,6-O-benzylidene-3-C-cyano-2-deoxy-α-D-ribo-hexopyranoside 
• 67974-18-9 (2R,4aR,6S,8S,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-8-carbonitrile 
• 63598-31-2 methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 
• 77481-69-7 (2S,4aR,6R,8S,8aR)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 
• 77481-68-6 methyl-4,6-O-benzylidene-2-deoxy-β-D-threo-hexopyranosid-3-ulose 

Downstream Products

• 77481-73-3 (2S,4aR,6R,8R,8aR)-6-Methoxy-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ylamine 

Relevant academic research and scientific papers

AN APPROACH TO BRANCHED-CHAIN AMINO SUGARS, PARTICULARLY DERIVATIVES OF L-VANCOSAMINE (3-AMINO-2,3,6-TRIDEOXY-3-C-METHYL-L-lyxo-HEXOSE) ITS D ENANTIOMER, via THE CYANO-HYDRIN ROUTE

Methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose reacted with potassium cyanide under equilibrating conditions to give, initially, methyl 4,6-O-bezylidene-3-C-cyano-2-deoxy-α-D-ribo-hexopyranoside (7), which, because it reverted slowly to the thermodynamically stable D-arabino isomer, could be crystallised directly from the reaction mixture.The mesylate derived from the kinetic product 7 could be converted by published procedures into methyl 3-acetamido-2,3,6-trideoxy-3-C-methyl-α-D-arabino-hexopyranoside, which was transformed into methyl N-acetyl-α-D-vancosamidine on inversion of the configuration at C-4.A hexopyranosid-3-ulose gave the kinetic cyanohydrin and thence, via the spiro-aziridine 27, methyl 3-acetamido-2,3,6-trideoxy-3-C-methyl-α-L-arabino-hexopyranoside, a known precursor of methyl N-acetyl-α-L-vancosaminide.

Stereospecific access to branched-chain carbohydrate synthons.

Appropriate precursors for the synthesis of D-vancosamine and L-evernitrose have been stereospecifically obtained from methyl 4,6-O-benzylidene-2-deoxy-α- and β-D-threo-hexopyranosid-3-ulose.