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 | 191805-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: 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]pyrrole-2,5-dione
• CAS: 191805-04-6
• 化学式: C₂₈H₃₃NO₆Si
• 分子量: 507.659
• InChiKey: AQWYBXYCORWVCF-QONNDPFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  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 在 三氟乙酸 作用下， 反应 2.0h， 以51%的产率得到3-((2S,3S,4R)-3,4-Dihydroxy-4-hydroxymethyl-tetrahydro-furan-2-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 、 三氟乙酸酐 、 lithium iodide 作用下， 以 吡啶 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 三氟乙酸 为溶剂， 反应 44.25h， 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：

  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

• 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).
• 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).