(4S)-4-(tert-butyldimethylsilyloxy)-4-{(4R,5R)-5-[(1S)-1-(tert-butyldimethylsilyloxy)ethyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-but-2Z-enal | 502768-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S)-4-(tert-butyldimethylsilyloxy)-4-{(4R,5R)-5-[(1S)-1-(tert-butyldimethylsilyloxy)ethyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-but-2Z-enal
• 英文别名: (Z,4S)-4-[tert-butyl(dimethyl)silyl]oxy-4-[(4R,5R)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-enal
• CAS: 502768-78-7
• 化学式: C₂₃H₄₆O₅Si₂
• 分子量: 458.786
• InChiKey: AHBBKBXEKDTQNE-BXJRZZKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-(tert-butyldimethylsilyloxy)-4-{(4R,5R)-5-[(1S)-1-(tert-butyldimethylsilyloxy)ethyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-but-2Z-enal 在 Grubbs catalyst first generation 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (6R)-6-[(3S)-3-tert-butyldimethylsilyloxy-3-{(4R,5R)-5-[(1S)-1-(tert-butyldimethylsilyloxy)ethyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-prop-1Z-enyl]-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Stereoselective synthesis of spicigerolide

  摘要：

  The first total synthesis of the naturally occurring, cytotoxic lactone spicigerolide is described. The commercially available sugar L-rhamnose was the chiral starting materal. Key steps in the synthesis were an aldehyde two-carbon homologation via the Corey-Fuchs protocol, an asymmetric Brown-type aldehyde allylation and a ring-closing metathesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02588-1
• 作为产物：
  描述：

  4-(tert-butyldimethylsilyloxy)-4-{5-[1-(tert-butyldimethylsilyloxy)ethyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-byt-2-ynal 在 Lindlar's catalyst 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到(4S)-4-(tert-butyldimethylsilyloxy)-4-{(4R,5R)-5-[(1S)-1-(tert-butyldimethylsilyloxy)ethyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-but-2Z-enal
  参考文献：
  名称：

  Stereoselective Synthesis and Determination of the Cytotoxic Properties of Spicigerolide and Three of Its Stereoisomers

  摘要：

  Stereoselective syntheses of the naturally occurring, cytotoxic lactone spicigerolide and three nonnatural stereoisomers thereof are described. The commercially available sugar L-rhamnose was in all cases the chiral starting material. Key steps in each of these syntheses were asymmetric Brown allylations and ring-closing metatheses. The cytotoxic activities of the four lactones against a range of tumoral lines were then determined.

  DOI：

  10.1021/jo034470y

文献信息

• Stereoselective Synthesis and Determination of the Cytotoxic Properties of Spicigerolide and Three of Its Stereoisomers
  作者：Eva Falomir、Juan Murga、Purificación Ruiz、Miguel Carda、J. Alberto Marco、Rogelio Pereda-Miranda、Mabel Fragoso-Serrano、Carlos M. Cerda-García-Rojas

  DOI：10.1021/jo034470y

  日期：2003.7.1

  Stereoselective syntheses of the naturally occurring, cytotoxic lactone spicigerolide and three nonnatural stereoisomers thereof are described. The commercially available sugar L-rhamnose was in all cases the chiral starting material. Key steps in each of these syntheses were asymmetric Brown allylations and ring-closing metatheses. The cytotoxic activities of the four lactones against a range of tumoral lines were then determined.
• Stereoselective synthesis of spicigerolide
  作者：Eva Falomir、Juan Murga、Miguel Carda、J.Alberto Marco

  DOI：10.1016/s0040-4039(02)02588-1

  日期：2003.1

  The first total synthesis of the naturally occurring, cytotoxic lactone spicigerolide is described. The commercially available sugar L-rhamnose was the chiral starting materal. Key steps in the synthesis were an aldehyde two-carbon homologation via the Corey-Fuchs protocol, an asymmetric Brown-type aldehyde allylation and a ring-closing metathesis. (C) 2002 Elsevier Science Ltd. All rights reserved.