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Synthesis of dibekacin analogs containing 3-oxaand 3-aza-2,3,4-trideoxy-d-glycero-hexopyranose

✍ Scribed by Ryuji Kuwahara; Tsutomu Tsuchiya

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 946 KB
Volume: 293
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(96)00176-0

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✦ Synopsis

6-O-(3-

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-l-thio-o-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.

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