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-trityloxymethyl-tetrahydro-pyran-3-yl ester | 737788-41-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 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-trityloxymethyl-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3S,4S,5R,6R)-2-[(1S,2S,3R,4S,5S,6R)-5-hydroxy-2,3,4-tris(phenylmethoxy)-6-prop-2-enoxycyclohexyl]oxy-4,5-bis(phenylmethoxy)-6-(trityloxymethyl)oxan-3-yl] benzoate
• CAS: 737788-41-9
• 化学式: C₇₆H₇₄O₁₂
• 分子量: 1179.42
• InChiKey: NYXYIPFPULJJEB-ZOQBBRJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  88
• 可旋转键数：
  29
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  12

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-trityloxymethyl-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， 生成
  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：

  1-O-allyl-3,4,5-tri-O-benzyl-D-myo-inositol 、 (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-2-pent-4-enyloxy-2-phenyl-5-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran 在 N-碘代丁二酰亚胺 、 ytterbium(III) triflate 作用下， 以97%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-trityloxymethyl-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

文献信息

• Synthesis of a Lipomannan Component of the Cell-Wall Complex ofMycobacterium tuberculosis Is Based on Paulsen's Concept of Donor/Acceptor “Match”
  作者：K. N. Jayaprakash、Jun Lu、Bert Fraser-Reid

  DOI：10.1002/anie.200500505

  日期：2005.9.12