Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4,6-tris-benzyloxy-5-hydroxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester | 803737-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4,6-tris-benzyloxy-5-hydroxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester
• 英文别名: Bz(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(a1-6)[Bn(-3)][Bn(-4)]Man(a)-O-Bn；[(2S,3S,4S,5R,6R)-2-[[(2R,3R,4R,5S,6S)-5-hydroxy-3,4,6-tris(phenylmethoxy)oxan-2-yl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 803737-76-0
• 化学式: C₆₁H₆₂O₁₂
• 分子量: 987.156
• InChiKey: IYXYVQKMYUXNFS-LRDLTPTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  73
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  Benzoic acid (2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester 、 Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4,6-tris-benzyloxy-5-hydroxy-tetrahydro-pyran-2-ylmethoxy)-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， 反应 0.25h， 以49 mg的产率得到
  参考文献：
  名称：

  Jayaprakash; Fraser-Reid, Bert, Organic Letters, 2004, vol. 6, # 23, p. 4211 - 4214

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,6-tri-O-benzoyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) 在 N-碘代丁二酰亚胺 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 ytterbium(III) triflate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 Benzoic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,4,6-tris-benzyloxy-5-hydroxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Jayaprakash; Fraser-Reid, Bert, Organic Letters, 2004, vol. 6, # 23, p. 4211 - 4214

  摘要：

  DOI：

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.