Benzoic acid (2R,3S,4S,5R,6R)-2-((1S,2R,3S,4S,5R,6S)-2-allyloxy-4,5,6-tris-benzyloxy-3-hydroxy-cyclohexyloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester | 740806-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2R,3S,4S,5R,6R)-2-((1S,2R,3S,4S,5R,6S)-2-allyloxy-4,5,6-tris-benzyloxy-3-hydroxy-cyclohexyloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
• CAS: 740806-03-5
• 化学式: C₆₄H₆₆O₁₂
• 分子量: 1027.22
• InChiKey: SLFPDQPHYRHBAB-PEWGVULCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.41
• 重原子数：
  76.0
• 可旋转键数：
  26.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  129.6
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane 、 Benzoic acid (2R,3S,4S,5R,6R)-2-((1S,2R,3S,4S,5R,6S)-2-allyloxy-4,5,6-tris-benzyloxy-3-hydroxy-cyclohexyloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 在 N-碘代丁二酰亚胺 、 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到
  参考文献：
  名称：

  Synthesis of a key Mycobacterium tuberculosis biosynthetic phosphoinositide intermediate

  摘要：

  Regioselective mannosylations of a myoinositol acceptor diol are readily achieved by Lewis acid mediated iodinolysis of n-pentenyl ortho-esters. The procedure affords a psuedotrisaccharide to which the phosphoglyceryl and other lipid residues are added leading to the key biosynthetic intermediate of Mycobacterium species. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.103
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) 、 1-O-allyl-3,4,5-tri-O-benzyl-D-myo-inositol 在 N-碘代丁二酰亚胺 、 ytterbium(III) triflate 作用下， 以96%的产率得到Benzoic acid (2R,3S,4S,5R,6R)-2-((1S,2R,3S,4S,5R,6S)-2-allyloxy-4,5,6-tris-benzyloxy-3-hydroxy-cyclohexyloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of a key Mycobacterium tuberculosis biosynthetic phosphoinositide intermediate

  摘要：

  Regioselective mannosylations of a myoinositol acceptor diol are readily achieved by Lewis acid mediated iodinolysis of n-pentenyl ortho-esters. The procedure affords a psuedotrisaccharide to which the phosphoglyceryl and other lipid residues are added leading to the key biosynthetic intermediate of Mycobacterium species. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.04.103