Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-trityloxymethyl-tetrahydro-pyran-3-yl ester | 737788-38-4

• 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 (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-pent-4-enyloxy-6-trityloxymethyl-tetrahydro-pyran-3-yl ester
• CAS: 737788-38-4
• 化学式: C₅₁H₅₀O₇
• 分子量: 774.954
• InChiKey: PITDFCHRFNCQLI-ULSKWHDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  58.0
• 可旋转键数：
  19.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 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-2-pent-4-enyloxy-6-trityloxymethyl-tetrahydro-pyran-3-yl ester 在 sodium methylate 作用下， 生成 (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-2-pent-4-enyloxy-6-trityloxymethyl-tetrahydro-pyran-3-ol
  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-5-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran 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-2-pent-4-enyloxy-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

• Efficient Chemical Synthesis of a Dodecasaccharidyl Lipomannan Component of Mycobacterial Lipoarabinomannan
  作者：Bert Fraser-Reid、Siddhartha Ray Chaudhuri、K. N. Jayaprakash、Jun Lu、Changalvala V. S. Ramamurty

  DOI：10.1021/jo802000p

  日期：2008.12.19

  Lipomannan (LM) is one of the domains of lipoarabinomannan (LAM) glycolipids, the latter being one of several cell surface organic molecules that fortify mycobacterial species against external attack. Some members of mycobacterial families are pathogenic, most notably Mycobacterium tuberculosis and Mycobacterium leprae, while others are nonpathogenic, and used in the clinic, such as Mycobacterium smegmatis. Additional biological significance arises from the fact that LM has been implicated in several health disorders outside of those associated with mycobacterial pathogens, notably for treatment of bladder cancer. LM is comprised of a heavily lipidated phosphoinositide dimannoside headgroup, from which a mannan array, of varied complexity, extends. The latter consists of a 1,6-alpha-linked backbone flanked at position O2, not necessarily regularly, with alpha-linked mannosides. This paper gives an example of lipomannan synthesis in which all of the sugar components, whether functioning as donors or acceptors, are obtained from n-pentenyl orthoesters, themselves in turn prepared in three easy steps from D-mannose. Assembly of the mannan array is facilitated by the exquisite regioselectivity occasioned by the use of ytterbium triflate/N-iodosuccinimide as the trigger for reaction of n-pentenyl orthoesters.