(E)-(5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-6-methyl-oct-2-enoic acid methyl ester | 218268-92-9

• 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: (E)-(5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-6-methyl-oct-2-enoic acid methyl ester
• 英文别名: methyl (E,5S,6R)-5-[tert-butyl(dimethyl)silyl]oxy-8-hydroxy-6-methyloct-2-enoate
• CAS: 218268-92-9
• 化学式: C₁₆H₃₂O₄Si
• 分子量: 316.513
• InChiKey: ZCRQSNXZXHWIPT-OJYSIEITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  (E)-(5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-hydroxy-6-methyl-oct-2-enoic acid methyl ester 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 作用下， 生成 (E)-(5S,6R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-8-oxo-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：

  (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

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.