Carbohydrate Research p. 207 - 216 (1982)
Update date:2022-08-02
Topics: Derivatization Purification Starting Material Scale-up Stereochemistry Control Analysis and Characterization Ring Formation Amino Group Introduction
Brimacombe, John S.
Mengech, Annalee S.
Rahman, Khandker M. M.
Tucker, Leslie C. N.
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.
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