(2S,3S,5S)-benzyl 2-hexyl-3-hydroxy-5-(benzyloxy)hexadecanoate | 134360-69-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3S,5S)-benzyl 2-hexyl-3-hydroxy-5-(benzyloxy)hexadecanoate
• 英文别名: benzyl (2S,3S,5S)-2-hexyl-3-hydroxy-5-phenylmethoxyhexadecanoate
• CAS: 134360-69-3
• 化学式: C₃₆H₅₆O₄
• 分子量: 552.838
• InChiKey: CTTRBKLILJWMLC-IMKBVMFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  40
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,5S)-benzyl 2-hexyl-3-hydroxy-5-(benzyloxy)hexadecanoate 在 吡啶 、 sodium hydroxide 、 苯磺酰氯 作用下， 以 乙醇 为溶剂， 反应 21.0h， 生成 (3S,4S,2'S)-3-hexyl-4-(2'-benzyloxytridec-1'-yl)oxetan-2-one
  参考文献：
  名称：

  Synthesis of tetrahydrolipstatin

  摘要：

  An asymmetric synthesis of tetrahydrolipstatin (4) is described. Application of our previously described in situ cyclopentadiene alkylation-asymmetric hydroboration protocol provided the key chiral alcohol 9. In the course of this work, the presence of a free hydroxyl group was found to exert a strong directing effect on the regioselectivity of a Baeyer-Villiger reaction (16 --> 17). Subsequent transformations of lactone 17 produced tetrahydrolipstatin (4).

  DOI：

  10.1021/jo00015a027
• 作为产物：
  描述：

  2,2,2-三氯乙酰胺苄酯 在 三氟甲磺酸 、 氢氟酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 乙腈 为溶剂， 反应 7.0h， 生成 (2S,3S,5S)-benzyl 2-hexyl-3-hydroxy-5-(benzyloxy)hexadecanoate
  参考文献：
  名称：

  Synthesis of tetrahydrolipstatin

  摘要：

  An asymmetric synthesis of tetrahydrolipstatin (4) is described. Application of our previously described in situ cyclopentadiene alkylation-asymmetric hydroboration protocol provided the key chiral alcohol 9. In the course of this work, the presence of a free hydroxyl group was found to exert a strong directing effect on the regioselectivity of a Baeyer-Villiger reaction (16 --> 17). Subsequent transformations of lactone 17 produced tetrahydrolipstatin (4).

  DOI：

  10.1021/jo00015a027

文献信息

• CHADHA, N. K.;BATCHO, A. D.;TANG, P. C.;COURTNEY, L. F.;COOK, C. M.;WOVKU+, J. ORG. CHEM., 56,(1991) N5, C. 4714-4718
  作者：CHADHA, N. K.、BATCHO, A. D.、TANG, P. C.、COURTNEY, L. F.、COOK, C. M.、WOVKU+

  DOI：——

  日期：——
• Synthesis of tetrahydrolipstatin
  作者：N. K. Chadha、A. D. Batcho、P. C. Tang、L. F. Courtney、C. M. Cook、P. M. Wovkulich、Milan R. Uskokovic

  DOI：10.1021/jo00015a027

  日期：1991.7

  An asymmetric synthesis of tetrahydrolipstatin (4) is described. Application of our previously described in situ cyclopentadiene alkylation-asymmetric hydroboration protocol provided the key chiral alcohol 9. In the course of this work, the presence of a free hydroxyl group was found to exert a strong directing effect on the regioselectivity of a Baeyer-Villiger reaction (16 --> 17). Subsequent transformations of lactone 17 produced tetrahydrolipstatin (4).