(Z)-(5R,8R)-5-Hydroxy-6-methyl-3-oxo-8-triisopropylsilanyloxymethyl-dec-6-enoic acid ethyl ester | 907593-88-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (Z)-(5R,8R)-5-Hydroxy-6-methyl-3-oxo-8-triisopropylsilanyloxymethyl-dec-6-enoic acid ethyl ester
• 英文别名: ethyl (Z,5R,8R)-5-hydroxy-6-methyl-3-oxo-8-[tri(propan-2-yl)silyloxymethyl]dec-6-enoate
• CAS: 907593-88-8
• 化学式: C₂₃H₄₄O₅Si
• 分子量: 428.685
• InChiKey: HABVLKDQJIVPBG-GXAKAIMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-(5R,8R)-5-Hydroxy-6-methyl-3-oxo-8-triisopropylsilanyloxymethyl-dec-6-enoic acid ethyl ester 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (Z)-(5S,8R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-6-methyl-8-triisopropylsilanyloxymethyl-dec-6-enoic acid ethyl ester
  参考文献：
  名称：

  A stereoselective synthesis of the C11–C19 fragment of (+)-peloruside A

  摘要：

  A new route to the synthesis of the C I I-C 19 fragment of peloruside A is described, which includes an aldol reaction with ethyl acetoacetate, P-hydroxyl-directed reduction of P-hydroxy ketone, as well as methylation of C 13 hydroxyl moiety in the system of Mel-Ag2O-MgSO4-CH2Cl2. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.135
• 作为产物：
  描述：

  ethyl (Z,4R)-2-methyl-4-[tri(propan-2-yl)silyloxymethyl]hex-2-enoate 在 sodium hydride 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (Z)-(5R,8R)-5-Hydroxy-6-methyl-3-oxo-8-triisopropylsilanyloxymethyl-dec-6-enoic acid ethyl ester
  参考文献：
  名称：

  A stereoselective synthesis of the C11–C19 fragment of (+)-peloruside A

  摘要：

  A new route to the synthesis of the C I I-C 19 fragment of peloruside A is described, which includes an aldol reaction with ethyl acetoacetate, P-hydroxyl-directed reduction of P-hydroxy ketone, as well as methylation of C 13 hydroxyl moiety in the system of Mel-Ag2O-MgSO4-CH2Cl2. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.135

文献信息

• A stereoselective synthesis of the C11–C19 fragment of (+)-peloruside A
  作者：Zhen-liang Chen、Wei-shan Zhou

  DOI：10.1016/j.tetlet.2006.05.135

  日期：2006.7

  A new route to the synthesis of the C I I-C 19 fragment of peloruside A is described, which includes an aldol reaction with ethyl acetoacetate, P-hydroxyl-directed reduction of P-hydroxy ketone, as well as methylation of C 13 hydroxyl moiety in the system of Mel-Ag2O-MgSO4-CH2Cl2. (c) 2006 Elsevier Ltd. All rights reserved.