64 EVERNINOMICIN中の新しい分枝糖の合成
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Four new branched-chain sugars, D-evermicose (1, 2,6-dideoxy-3-C-methyl-D-arabinohexose), L-evernitrose (2, 2,3,6-trideoxy-3-C-methyl-4-O-methyl-3-nitro-L-arabino-hexose), D-evalose (3, 6-deoxy-3-C-methyl-D-mannose), and 6-Deoxy-4-C-hydroxymethyl-5-O-methyl-2,3-O-methylene-L-idono-6,4^L lactone (4) are components of oligosaccharide antibiotics, everninomicins B, C and D. We have synthesized these new branched-chain sugars. Synthesis of (1) was achieved in four steps from methyl 4,6-O-benzylidene-2-deoxy-3-C-methyl-α-D-arabino-hexopyranoside (11), which was prepared from (5) and (9) by two different methods. (2) and its enantiomer were synthesized from methyl 2,6-dideoxy-4-O-methyl-α-L-erythro-hexopyranosid-3-ulose (16) and methyl 4,6-O-benzylidene-2-deoxy-α-D-erythro-hexopyranosid-3-ulose (15), respectively. In both cases, the unique nitro group attached to the tertiary branching carbon was introduced by oxidation of corresponding amino derivatives prepared by Bourgeois's method. (3) was synthesized from methyl 3,3'-anhydro-4,6-O-benzylidene-3-C-hydroxymethyl-2-O-methyl-α-D-mannopyranoside (31) through five-step derivations. Grignard reactions of benzyl 2,3-di-O-benzyl (37a)and 2,3-O-methylene-β-L-erythro-pentopyranosid-4-ulose (37b)with CH_2=CHMgBr, followed by peroxide oxidation of double bonds and LiAlH_4 reduction, gave benzyl 2,3-di-O-benzyl-6-deoxy-4-C-hydroxymethyl-L-idoside and the corresponding 2,3-O-methylene derivative, whose conversions into (4) are under investigation.
- 天然有機化合物討論会の論文
- 1979-09-20
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