Canadian Journal of Chemistry

Chlorosulphation of amino sugars: synthesis of methyl 2-acetamido-4-amino-2, 4, 6-trideoxy-β-d-glucopyranoside (bacillosamine) from a d-glucosamine derivative

DR Bundle, S Josephson

文献索引：Bundle, David R.; Josephson, Staffan Canadian Journal of Chemistry, 1980 , vol. 58, p. 2679 - 2685

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被引用次数: 22

摘要

Chlorosulphation of methyl 2-deoxy-2-phthalimido-β-d-glucopyranoside 3 under controlled conditions provided either methyl 6-chloro-2, 6-dideoxy-2-phthalimido-β-d-glucopyranoside 4 or methyl 4, 6-dichloro-2, 4, 6-trideoxy-2-phthalimido-β-d-galactopyranoside 5. Chlorination at C-4 occurs to the exclusion of that at C-3, in sharp contrast to the chlorosulphation of methyl β-d-glucopyranoside which is known to give both the 4, 6- ...