[(2R,4aR,6R,7R,8S,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-yl] acetate | 1007886-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,4aR,6R,7R,8S,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-yl] acetate
• CAS: 1007886-04-5
• 化学式: C₄₉H₄₈ClIO₁₂
• 分子量: 991.27
• InChiKey: WKPOUKHVGKZNGG-AOXQTXQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  63
• 可旋转键数：
  15
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3-O-benzyl-4,6;4',6'-di-O-benzylidene-3'-O-(p-chlorobenzyl)-2'-O-(p-iodobenzyl)-α,α-D-trehalose 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 以0.100 g的产率得到[(2R,4aR,6R,7R,8S,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-yl] acetate
  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