(5S,6S,7R,8R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-(2,2-dimethyl-propionyloxymethyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid | 642409-82-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: (5S,6S,7R,8R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-(2,2-dimethyl-propionyloxymethyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid
• 英文别名: (5S,6S,7R,8R)-5-[tert-butyl(dimethyl)silyl]oxy-8-[4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethoxyphenyl]-7-(2,2-dimethylpropanoyloxymethyl)-5,6,7,8-tetrahydrobenzo[f][1,3]benzodioxole-6-carboxylic acid
• CAS: 642409-82-3
• 化学式: C₃₈H₅₈O₁₀Si₂
• 分子量: 731.044
• InChiKey: DRCQAJVUZDQDQX-BESSAKRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.93
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (5S,6S,7R,8R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-(2,2-dimethyl-propionyloxymethyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙基硼氢化锂 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 11-oxo-13-deoxo-4'-benzyloxycarbonyl-4'-demethylepipodophyllotoxin
  参考文献：
  名称：

  Synthesis and antiproliferative activity of retroetoposide

  摘要：

  Retro-4'-demethyl-4-epipodophyllotoxin 6 was synthesized in eight steps and 10% overall yield from 4'-demethyl-4-epipodophyllotoxin 12. Subsequent coupling of 22 with 1-O-trimethylsilyl-4,6-O-ethylidene-beta-D-glucoside 26 afforded retroetoposide 5 which is 10-fold less cytotoxic than etoposide against L1210 cell line. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.044
• 作为产物：
  描述：

  4'-去甲基表鬼臼毒素 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium chlorite 、 lithium aluminium tetrahydride 、 氨基磺酸 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 4.0h， 生成 (5S,6S,7R,8R)-5-(tert-Butyl-dimethyl-silanyloxy)-8-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-phenyl]-7-(2,2-dimethyl-propionyloxymethyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid
  参考文献：
  名称：

  Synthesis and antiproliferative activity of retroetoposide

  摘要：

  Retro-4'-demethyl-4-epipodophyllotoxin 6 was synthesized in eight steps and 10% overall yield from 4'-demethyl-4-epipodophyllotoxin 12. Subsequent coupling of 22 with 1-O-trimethylsilyl-4,6-O-ethylidene-beta-D-glucoside 26 afforded retroetoposide 5 which is 10-fold less cytotoxic than etoposide against L1210 cell line. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.044

文献信息

• Synthesis and antiproliferative activity of retroetoposide
  作者：Philippe Meresse、Prokopios Magiatis、Emmanuel Bertounesque、Claude Monneret

  DOI：10.1016/j.bmcl.2003.08.044

  日期：2003.11

  Retro-4'-demethyl-4-epipodophyllotoxin 6 was synthesized in eight steps and 10% overall yield from 4'-demethyl-4-epipodophyllotoxin 12. Subsequent coupling of 22 with 1-O-trimethylsilyl-4,6-O-ethylidene-beta-D-glucoside 26 afforded retroetoposide 5 which is 10-fold less cytotoxic than etoposide against L1210 cell line. (C) 2003 Elsevier Ltd. All rights reserved.