(3aS,4R,6aR)-6a-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester | 191805-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4R,6aR)-6a-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester
• 英文别名: methyl (3aR,6R,6aS)-3a-(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxole-6-carboxylate
• CAS: 191805-00-2
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: CRHZOEOZPAFMDL-MATHAZKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aS,4R,6aR)-6a-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester 在 咪唑 、 4-二甲氨基吡啶 、 氯化亚砜 、 lithium iodide 作用下， 以 吡啶 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.25h， 生成 (3aS,4R,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl chloride
  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：

  1,3'-di-O-acetyl-2,3-O-isopropylidene-D-apio-β-D-furanose 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 反应 49.5h， 生成 (3aS,4R,6aR)-6a-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl 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).