((3aS,6S,6aR)-6-Bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-tert-butyl-diphenyl-silane | 196808-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3aS,6S,6aR)-6-Bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-tert-butyl-diphenyl-silane
• 英文别名: [(3aS,6S,6aR)-6-bromo-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-3a-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 196808-03-4
• 化学式: C₂₄H₃₁BrO₄Si
• 分子量: 491.497
• InChiKey: GWLHJBCFLRGFST-IMSXRSKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((3aS,6S,6aR)-6-Bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-tert-butyl-diphenyl-silane 在 sodium periodate 、 正丁基锂 、 苯基氯化硒 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 N-环己基异丙基胺 、 双氧水 、 sodium carbonate 作用下， 反应 2.0h， 生成 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：

  A second synthesis ofD-apio-?-D-furanosyl maleimide as a structural analogue of showdomycin

  摘要：

  Apioshowdomycin (3-(D-apio-4-D-furanosyl)-1H-pyrrole-2,5-dione, 2) has been pre pared as an analogue of the C-nucleoside showdomycin (1) in seven steps. starting from 2,3-O-isopropylidene-D-apio-D-furanose (8). The key step is the addition of a radical generated from apiosyl bromide 5b to (E)-methyl 3-cyanoacrylate (4).

  DOI：

  10.1007/bf00807603
• 作为产物：
  描述：

  Benzoic acid (3aR,6aS)-6a-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester 在 三甲基溴硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 ((3aS,6S,6aR)-6-Bromo-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-3a-ylmethoxy)-tert-butyl-diphenyl-silane
  参考文献：
  名称：

  A second synthesis ofD-apio-?-D-furanosyl maleimide as a structural analogue of showdomycin

  摘要：

  Apioshowdomycin (3-(D-apio-4-D-furanosyl)-1H-pyrrole-2,5-dione, 2) has been pre pared as an analogue of the C-nucleoside showdomycin (1) in seven steps. starting from 2,3-O-isopropylidene-D-apio-D-furanose (8). The key step is the addition of a radical generated from apiosyl bromide 5b to (E)-methyl 3-cyanoacrylate (4).

  DOI：

  10.1007/bf00807603

文献信息

• A second synthesis ofD-apio-?-D-furanosyl maleimide as a structural analogue of showdomycin
  作者：M. Drescher、F. Hammerschmidt

  DOI：10.1007/bf00807603

  日期：——

  Apioshowdomycin (3-(D-apio-4-D-furanosyl)-1H-pyrrole-2,5-dione, 2) has been pre pared as an analogue of the C-nucleoside showdomycin (1) in seven steps. starting from 2,3-O-isopropylidene-D-apio-D-furanose (8). The key step is the addition of a radical generated from apiosyl bromide 5b to (E)-methyl 3-cyanoacrylate (4).