3-O-benzyl-4,6;4',6'-di-O-benzylidene-3'-O-(p-chlorobenzyl)-2'-O-(p-iodobenzyl)-α,α-D-trehalose | 1007885-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-benzyl-4,6;4',6'-di-O-benzylidene-3'-O-(p-chlorobenzyl)-2'-O-(p-iodobenzyl)-α,α-D-trehalose
• 英文别名: (2R,4aR,6R,7R,8R,8aR)-6-[[(2R,4aR,6R,7R,8S,8aR)-8-[(4-chlorophenyl)methoxy]-7-[(4-iodophenyl)methoxy]-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 1007885-90-6
• 化学式: C₄₇H₄₆ClIO₁₁
• 分子量: 949.233
• InChiKey: KAUHERRCFJSYEG-XFHGUNBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  60
• 可旋转键数：
  13
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-4,6;4',6'-di-O-benzylidene-3'-O-(p-chlorobenzyl)-2'-O-(p-iodobenzyl)-α,α-D-trehalose 、 1-(碘甲基)-4-甲氧基苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以4.15 g的产率得到3-O-benzyl-4,6;4',6'-di-O-benzylidene-3'-O-(p-chlorobenzyl)-2'-O-(p-iodobenzyl)-2-O-(p-methoxybenzyl)-α,α-D-trehalose
  参考文献：
  名称：

  Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I

  摘要：

  [GRAPHICS]Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.

  DOI：

  10.1021/jo702032c
• 作为产物：
  描述：

  在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 三氟甲烷磺酸甲酯 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 3-O-benzyl-4,6;4',6'-di-O-benzylidene-3'-O-(p-chlorobenzyl)-2'-O-(p-iodobenzyl)-α,α-D-trehalose
  参考文献：
  名称：

  Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I

  摘要：

  [GRAPHICS]Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.

  DOI：

  10.1021/jo702032c