Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester | 737788-39-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester
• CAS: 737788-39-5
• 化学式: C₃₈H₅₀O₇Si
• 分子量: 646.896
• InChiKey: CGQCDAWSCQSBSX-PUCOHDNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.11
• 重原子数：
  46.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-pent-4-enyloxy-tetrahydro-pyran-3-yl ester 在 sodium methylate 作用下， 生成 tert-Butyl-dimethyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane
  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：

  ((3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-2-pent-4-enyloxy-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-5-ylmethoxy)-tert-butyl-dimethyl-silane 在 ytterbium(III) triflate 作用下， 以100%的产率得到Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-pent-4-enyloxy-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