(2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-2-methyl-tetrahydro-pyran | 764696-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-2-methyl-tetrahydro-pyran
• CAS: 764696-76-6
• 化学式: C₆₈H₇₂N₁₂O₁₁
• 分子量: 1233.39
• InChiKey: JELPIKPGZZZMJA-NLJZYGGQSA-N

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-2-methyl-tetrahydro-pyran 在 三氟甲磺酸三甲基硅酯 、 乙酸酐 、 sodium methylate 作用下， 以 甲醇 为溶剂， 以25%的产率得到{(2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-2-methyl-tetrahydro-pyran-2-yl}-methanol
  参考文献：
  名称：

  Synthesis of an unusual branched-chain sugar, 5-C-methyl-l-idopyranose for SAR studies of pyranmycins: implication for the future design of aminoglycoside antibiotics

  摘要：

  The syntheses of a challenging branched-chain sugar and several L-sugars have been accomplished. Their application in studies of the antibacterial activity of pyranmycins is reported, which could provide new strategies for the future design of aminoglycoside antibiotics. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.064
• 作为产物：
  描述：

  Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-2-acetoxymethyl-6-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-2-methyl-tetrahydro-pyran-3-yl ester 在 甲醇 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[(1R,2R,3S,5R,6S)-3,5-diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-2-methyl-tetrahydro-pyran
  参考文献：
  名称：

  Synthesis of an unusual branched-chain sugar, 5-C-methyl-l-idopyranose for SAR studies of pyranmycins: implication for the future design of aminoglycoside antibiotics

  摘要：

  The syntheses of a challenging branched-chain sugar and several L-sugars have been accomplished. Their application in studies of the antibacterial activity of pyranmycins is reported, which could provide new strategies for the future design of aminoglycoside antibiotics. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.064