(4R,6R)-4-Hydroxy-6-((Z)-(R)-1-methyl-3-triisopropylsilanyloxymethyl-pent-1-enyl)-tetrahydro-pyran-2-one | 907593-93-5

• 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: (4R,6R)-4-Hydroxy-6-((Z)-(R)-1-methyl-3-triisopropylsilanyloxymethyl-pent-1-enyl)-tetrahydro-pyran-2-one
• 英文别名: (4R,6R)-4-hydroxy-6-[(Z,4R)-4-[tri(propan-2-yl)silyloxymethyl]hex-2-en-2-yl]oxan-2-one
• CAS: 907593-93-5
• 化学式: C₂₁H₄₀O₄Si
• 分子量: 384.632
• InChiKey: JFZFKAZHVIQXMO-JNWCFWDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  (4R,6R)-4-Hydroxy-6-((Z)-(R)-1-methyl-3-triisopropylsilanyloxymethyl-pent-1-enyl)-tetrahydro-pyran-2-one 在 4-甲基苯磺酸吡啶 、 magnesium sulfate 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-(3R,5R,8R)-5-Hydroxy-3-methoxy-6-methyl-8-triisopropylsilanyloxymethyl-dec-6-enoic acid methyl 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：

  (Z)-(3R,5R,8R)-3,5-Dihydroxy-6-methyl-8-triisopropylsilanyloxymethyl-dec-6-enoic acid ethyl ester 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到(4R,6R)-4-Hydroxy-6-((Z)-(R)-1-methyl-3-triisopropylsilanyloxymethyl-pent-1-enyl)-tetrahydro-pyran-2-one
  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.