(E)-3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-acrylic acid tert-butyl ester | 191805-03-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-acrylic acid tert-butyl ester
• 英文别名: tert-butyl (E)-3-[(3aS,6S,6aS)-3a-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-6-yl]-3-cyanoprop-2-enoate
• CAS: 191805-03-5
• 化学式: C₃₂H₄₁NO₆Si
• 分子量: 563.766
• InChiKey: ABVLIODQXGIZQN-DBTJHLCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  87
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-acrylic acid tert-butyl ester 在 三氟乙酸酐 作用下， 以 三氟乙酸 为溶剂， 反应 6.0h， 以42%的产率得到3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis ofD-apio-?-D-furanosyl maleimide, an analogue of showdomycin with transposed hydroxymethyl group

  摘要：

  Apioshowdomycin (3-(D-apio-beta-D-furanosyl)-1H-pynole-2,5-dione, 2) has been prepared as an analogue of the C-nucleoside showdomycin (1) in eight steps and with 5% overall yield, starting from 2,3-O-isopropylidene-D-apio-beta-D-furanose (3).

  DOI：

  10.1007/bf00807307
• 作为产物：
  描述：

  Acetic acid (3aS,6S,6aS)-6-cyano-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethyl ester 在 咪唑 、 4-二甲氨基吡啶 、 氯化亚砜 、 sodium methylate 、 lithium iodide 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.25h， 生成 (E)-3-[(3aS,4S,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3-cyano-acrylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis ofD-apio-?-D-furanosyl maleimide, an analogue of showdomycin with transposed hydroxymethyl group

  摘要：

  Apioshowdomycin (3-(D-apio-beta-D-furanosyl)-1H-pynole-2,5-dione, 2) has been prepared as an analogue of the C-nucleoside showdomycin (1) in eight steps and with 5% overall yield, starting from 2,3-O-isopropylidene-D-apio-beta-D-furanose (3).

  DOI：

  10.1007/bf00807307

文献信息

• Synthesis ofD-apio-?-D-furanosyl maleimide, an analogue of showdomycin with transposed hydroxymethyl group
  作者：F. Hammerschmidt、B. Peric、E. �hler

  DOI：10.1007/bf00807307

  日期：1997.2

  Apioshowdomycin (3-(D-apio-beta-D-furanosyl)-1H-pynole-2,5-dione, 2) has been prepared as an analogue of the C-nucleoside showdomycin (1) in eight steps and with 5% overall yield, starting from 2,3-O-isopropylidene-D-apio-beta-D-furanose (3).