Acetic acid (R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-((3aR,4R,6aR)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl ester | 115040-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-((3aR,4R,6aR)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl ester
• 英文别名: [(R)-[(3aR,6R,6aR)-2,2-dimethyl-4-oxo-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-6-yl]-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl] acetate
• CAS: 115040-58-9
• 化学式: C₁₅H₂₂O₈
• 分子量: 330.335
• InChiKey: LGEYBEOHLCBXRQ-RMPHRYRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid (R)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-((3aR,4R,6aR)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl ester 在 镍 、 三(二甲胺基)膦 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 6-O-acetyl-2,5-anhydro-1-deoxy-3,4:7,8-di-O-isopropylidene-D-erythro-L-galacto-octitol
  参考文献：
  名称：

  Dichloromethylenation of 1,4-lactones. A new access to 1-deoxy-1-C-methyl-C-glycosyl compounds

  摘要：

  DOI：

  10.1016/s0008-6215(00)90875-9

文献信息

• Dichloromethylenation of Lactones. 6. Efficient Synthesis of Dichloroolefins from Lactones and Acetates Using Triphenylphosphine and Tetrachloromethane
  作者：Mohamed Lakhrissi、Yves Chapleur

  DOI：10.1021/jo00098a039

  日期：1994.9

  Triphenylphosphine and tetrachloromethane react cleanly in refluxing tetrahydrofuran with substituted gamma and delta-lactones and some esters to afford the corresponding dichloroolefins in good yields. This new Wittig-type reaction provides an easy entry to this new class of compounds and tolerates a large variety of protecting groups. Application of this methodology to the dichloroolefination of simple lactones, sugar-derived lactones, and other biologically significant lactones is described.
• Facile dibromoolefination of lactones using bromomethylenetriphenylphosphorane
  作者：Younès Lakhrissi、Claude Taillefumier、Françoise Chrétien、Yves Chapleur

  DOI：10.1016/s0040-4039(01)01531-3

  日期：2001.10

  Dibromoolefination of lactones was achieved in high yields using bromomethylenetriphenylphosphorane in refluxing tetrahydrofuran. This reaction is believed to proceed via bromination of the monobromophosphorane from the corresponding bromomethyltriphenylphosphonium bromide with concomitant formation of methylenetriphenylphosphorane as shown by P-31 NMR. Transylidation should Occur to afford the reactive dibromomethylenetriphenylphosphorane. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Lakhrissi, Mohammed; Chapleur, Yves, Angewandte Chemie, 1996, vol. 108, # 7, p. 833 - 834
  作者：Lakhrissi, Mohammed、Chapleur, Yves

  DOI：——

  日期：——