64 EVERNINOMICIN中の新しい分枝糖の合成

• 松沢 政文

  東工大・理

• 洪 南基

  東工大・理

• 吉村 寿次

  東工大・理

書誌事項

タイトル別名

• 64 SYNTHESIS OF NEW BRANCHED-CHAIN SUGARS ISOLATED FROM EVERNINOMICINS

抄録

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.

収録刊行物

• 天然有機化合物討論会講演要旨集

  天然有機化合物討論会講演要旨集 22 (0), 485-492, 1979

  天然有機化合物討論会実行委員会

詳細情報

• CRID: 1390001206072665984
• NII論文ID: 110006678091
• DOI: 10.24496/tennenyuki.22.0_485
• ISSN: 24331856
• 本文言語コード: ja
• データソース種別:
  • JaLC
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可