(3S,4S,6S)-4-<(tert-butyldimethylsilyl)oxy>-3-hexyl-6-undecyltetrahydro-2H-pyran-2-one | 134360-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4S,6S)-4-<(tert-butyldimethylsilyl)oxy>-3-hexyl-6-undecyltetrahydro-2H-pyran-2-one
• 英文别名: (3S,4S,6S)-4-[tert-butyl(dimethyl)silyl]oxy-3-hexyl-6-undecyloxan-2-one
• CAS: 134360-67-1
• 化学式: C₂₈H₅₆O₃Si
• 分子量: 468.836
• InChiKey: SADDCMOSKFSCRX-GSDHBNRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  32
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S,6S)-4-<(tert-butyldimethylsilyl)oxy>-3-hexyl-6-undecyltetrahydro-2H-pyran-2-one 在 吡啶 、 氢氧化钾 、 sodium hydroxide 、 三氟甲磺酸 、 氢氟酸 、 苯磺酰氯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 环己烷 、 乙腈 为溶剂， 反应 45.33h， 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：

  3-己基-4-羟基-6-十一烷基四氢-2H-吡喃-2-酮 、 叔丁基二甲基氯硅烷 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以90%的产率得到(3S,4S,6S)-4-<(tert-butyldimethylsilyl)oxy>-3-hexyl-6-undecyltetrahydro-2H-pyran-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

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).