3-(tert-butyldimethylsilanyloxy)hexadecanoic acid 3-<3-(tert-butyldimethylsilanyloxy)hexadecanoyloxy>-2-hydroxypropyl ester | 245489-87-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 3-(tert-butyldimethylsilanyloxy)hexadecanoic acid 3-<3-(tert-butyldimethylsilanyloxy)hexadecanoyloxy>-2-hydroxypropyl ester
• 英文别名: [3-[(3R)-3-[tert-butyl(dimethyl)silyl]oxyhexadecanoyl]oxy-2-hydroxypropyl] (3R)-3-[tert-butyl(dimethyl)silyl]oxyhexadecanoate
• CAS: 245489-87-6
• 化学式: C₄₇H₉₆O₇Si₂
• 分子量: 829.446
• InChiKey: GPMYSHUQIARATE-OCQXTOTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  56.0
• 可旋转键数：
  36.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-(tert-butyldimethylsilanyloxy)hexadecanoic acid 3-<3-(tert-butyldimethylsilanyloxy)hexadecanoyloxy>-2-hydroxypropyl ester 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以72%的产率得到3-hydroxyhexadecanoic acid 2-hydroxy-3-(3-hydroxyhexadecanoyloxy)propyl ester
  参考文献：
  名称：

  Enantioselective synthesis of natural biologically active ivaide A: 1,3-di-(R)-β-hydroxy-glyceride glycerol

  摘要：

  The natural 1,3-di-beta-hydroxy-glyceride glycerol ivaide A 1 from Ajuga iva has been synthesised by diacylation of dihydroxyacetone with 3-hydroxyhexadecanoic acid, followed by reduction to the corresponding glycerol derivative. The enantiomerically pure (R)-beta-hydroxyhexadecanoic ester intermediate 6 was obtained by a coupling reaction of an ethylacetoacetate dianion and the corresponding bromoalkyl, followed by the known reduction of the resulting beta-ketoester 5 by fermenting baker's yeast. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00222-0
• 作为产物：
  描述：

  (R)-3-hydroxyhexadecanoic acid ethyl ester 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 57.17h， 生成 3-(tert-butyldimethylsilanyloxy)hexadecanoic acid 3-<3-(tert-butyldimethylsilanyloxy)hexadecanoyloxy>-2-hydroxypropyl ester
  参考文献：
  名称：

  Enantioselective synthesis of natural biologically active ivaide A: 1,3-di-(R)-β-hydroxy-glyceride glycerol

  摘要：

  The natural 1,3-di-beta-hydroxy-glyceride glycerol ivaide A 1 from Ajuga iva has been synthesised by diacylation of dihydroxyacetone with 3-hydroxyhexadecanoic acid, followed by reduction to the corresponding glycerol derivative. The enantiomerically pure (R)-beta-hydroxyhexadecanoic ester intermediate 6 was obtained by a coupling reaction of an ethylacetoacetate dianion and the corresponding bromoalkyl, followed by the known reduction of the resulting beta-ketoester 5 by fermenting baker's yeast. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00222-0