(4R,5Z,7S)-7-(tert-butyldimethylsilyloxy)-7-{(4R,5R)-5-[(1S)-1-(tert-butyldimethylsilyloxy)ethyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-hepta-1,5-dien-4-ol | 502768-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5Z,7S)-7-(tert-butyldimethylsilyloxy)-7-{(4R,5R)-5-[(1S)-1-(tert-butyldimethylsilyloxy)ethyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-hepta-1,5-dien-4-ol
• 英文别名: (4R,5Z,7S)-7-[tert-butyl(dimethyl)silyl]oxy-7-[(4R,5R)-5-[(1S)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]hepta-1,5-dien-4-ol
• CAS: 502768-79-8
• 化学式: C₂₆H₅₂O₅Si₂
• 分子量: 500.867
• InChiKey: LABCJLDIUXXOSL-VMKNURRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5Z,7S)-7-(tert-butyldimethylsilyloxy)-7-{(4R,5R)-5-[(1S)-1-(tert-butyldimethylsilyloxy)ethyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-hepta-1,5-dien-4-ol 在 Grubbs catalyst first generation 甲醇 、 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (-)-spicigerolide
  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-[1-(tert-butyldimethylsilyloxy)-2,2-bis(ethylsulfanyl)ethyl]-5-[1-(tert-butyldimethylsilyloxy)ethyl]-2,2-dimethyl[1,3]dioxolane 在 Lindlar's catalyst 氢气 、 三苯基膦 、 乙腈 、 calcium carbonate 、 mercury dichloride 、 锌 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 (4R,5Z,7S)-7-(tert-butyldimethylsilyloxy)-7-{(4R,5R)-5-[(1S)-1-(tert-butyldimethylsilyloxy)ethyl]-2,2-dimethyl[1,3]dioxolan-4-yl}-hepta-1,5-dien-4-ol
  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

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.