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Synthesis of protected purpurosamine B and 6-epipurpurosamine B

✍ Scribed by Nobuyoshi Yasuda; Keiji Matsuda; Hideo Tsutsumi; Takao Takaya

Book ID: 102991124
Publisher: Elsevier Science
Year: 1986
Tongue: English
Weight: 754 KB
Volume: 146
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(86)85023-6

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✦ Synopsis

In relation to the synthesis of antipseudomonal drugs, namely, gentamicin C2 and 3-de-O-methylsporaricin A, a protected purpurosamine B (15) and 6-epipurpurosamine B (13) were synthesized. The key intermediate, methyl 2,3,4,7- tetradeoxy-6-O-(methylsulfonyl)-2-phthalimido-beta-L-lyxo-++ +heptopyranoside (8), was obtained in 48% yield by Grignard addition to methyl 2,3,4-trideoxy-2-phthalimido-alpha-D-erythro-hexodialdo-1,5-pyrano side (7) proceeding in accordance with Cram's chelate rule, followed by methylsulfonylation. From 8, compound 15 was readily obtained by introduction of the azide group with inversion of configuration at C-6. Compound 13 was obtained by introduction of the azide group with retention of configuration.

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