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Synthesis of kanamycin a analogs containing 6-amino-3-oxa-2,3,4,6-tetradeoxy-d- and -l-glycero-hexopyranose

✍ Scribed by Ryuji Kuwahara; Tsutomu Tsuchiya

Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 922 KB
Volume: 286
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(96)00051-1

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✦ Synopsis

6-Azido-3-oxa-2,3,4,6-tetradeoxy-D- and -L-glycero-hexopyranoses were synthesized in five steps from (2S)-and (2R)-1,2-O-isopropylideneglycerols, respectively. After conversion into the corresponding ethyl 1-thioglycosides, each was condensed with a protected derivative of 6-O-(3-amino-3-deoxy-alpha-D-glucopyranosyl)-2-deoxystreptamine (16). Deprotection and reduction of the azido group of the condensation products gave the title compounds.

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