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含3-氧杂-和3-氮杂-2,3,4-三脱氧-D-甘油-己吡喃糖的地贝卡星类似物的合成。

Synthesis of dibekacin analogs containing 3-oxa- and 3-aza-2,3,4-trideoxy-D-glycero-hexopyranose.

作者信息

Kuwahara R, Tsuchiya T

机构信息

Institute of Bioorganic Chemistry, Kawasaki, Japan.

出版信息

Carbohydr Res. 1996 Oct 23;293(1):15-20. doi: 10.1016/0008-6215(96)00176-0.

DOI:10.1016/0008-6215(96)00176-0
PMID:8916543
Abstract

6-O-(3-Oxa-2,3,4-trideoxy-alpha-D-glycero-hexopyranosyl) derivatives (10 and 17) of both 3',4'-dideoxyneamine and 5-epifluoro-5,3',4'-trideoxyneamine have been prepared by coupling ethyl 6-O-benzyl-3-oxa-2,3,4-trideoxy-1-thio-D-glycero-hexopyranoside (5) with suitable aglycons. The corresponding 3"-aza derivative (19) of dibekacin (6) was prepared by oxidation of 1,3,2',6'-tetra-N-tosyldibekacin (7) with Pb(OAc)4 followed by treatment with NH4OAc and reduction with NaBH3CN. Related ring-opening compounds (11 and 25) were also prepared.

摘要

通过将6-O-苄基-3-氧杂-2,3,4-三脱氧-1-硫代-D-甘油基己吡喃糖苷（5）与合适的苷元偶联，制备了3',4'-二脱氧新霉素胺和5-表氟-5,3',4'-三脱氧新霉素胺的6-O-(3-氧杂-2,3,4-三脱氧-α-D-甘油基己吡喃糖基)衍生物（10和17）。通过用Pb(OAc)4氧化1,3,2',6'-四-N-甲苯磺酰二贝卡星（7），然后用NH4OAc处理并用NaBH3CN还原，制备了二贝卡星（6）的相应3''-氮杂衍生物（19）。还制备了相关的开环化合物（11和25）。

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