(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-oxepan-2-one | 218268-87-2

• 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: (4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-oxepan-2-one
• 英文别名: (4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-methyloxepan-2-one
• CAS: 218268-87-2
• 化学式: C₁₃H₂₆O₃Si
• 分子量: 258.433
• InChiKey: HYRZFMPNQSIOIK-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  (4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-oxepan-2-one 在 1,1,2,3-四甲基胍 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (E)-(5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-6-methyl-oct-2-enoic acid methyl ester
  参考文献：
  名称：

  Bioreduction of (R)-carvone and regioselective Baeyer-Villiger oxidations: Application to the asymmetric synthesis of cryptophycin fragment A

  摘要：

  Cryptophycin fragment A (1) was prepared in high enantiomeric purity in 10 steps from(R)-carvone. A stereoselective bioreduction of (R)-carvone to neodihydrocarveol and a regioselective Baeyer-Villiger oxidation of cyclohexanone 8 with pertrifluoroacetic acid were employed in this synthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01784-5
• 作为产物：
  描述：

  (3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methyl-cyclohexanone 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以67%的产率得到(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-oxepan-2-one
  参考文献：
  名称：

  Bioreduction of (R)-carvone and regioselective Baeyer-Villiger oxidations: Application to the asymmetric synthesis of cryptophycin fragment A

  摘要：

  Cryptophycin fragment A (1) was prepared in high enantiomeric purity in 10 steps from(R)-carvone. A stereoselective bioreduction of (R)-carvone to neodihydrocarveol and a regioselective Baeyer-Villiger oxidation of cyclohexanone 8 with pertrifluoroacetic acid were employed in this synthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01784-5

文献信息

• Bioreduction of (R)-carvone and regioselective Baeyer-Villiger oxidations: Application to the asymmetric synthesis of cryptophycin fragment A
  作者：David L. Varie、John Brennan、Barbara Briggs、Jason S. Cronin、David A. Hay、John A. Rieck、Milton J. Zmijewski

  DOI：10.1016/s0040-4039(98)01784-5

  日期：1998.11

  Cryptophycin fragment A (1) was prepared in high enantiomeric purity in 10 steps from(R)-carvone. A stereoselective bioreduction of (R)-carvone to neodihydrocarveol and a regioselective Baeyer-Villiger oxidation of cyclohexanone 8 with pertrifluoroacetic acid were employed in this synthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.