5,6-O-Isopropylidene-2-O-allyl-3-O-methyl-L-ascorbic acid | 158598-26-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-O-Isopropylidene-2-O-allyl-3-O-methyl-L-ascorbic acid
• 英文别名: (2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methoxy-4-prop-2-enoxy-2H-furan-5-one
• CAS: 158598-26-6
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: VKSXRRURQAVDPJ-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-O-Isopropylidene-2-O-allyl-3-O-methyl-L-ascorbic acid 以 甲苯 为溶剂， 以82%的产率得到5,6-Isopropylidene-2-keto-3-O-methyl-3-(1-prop-2-enyl)-L-galactono-γ-lactone
  参考文献：
  名称：

  Chemistry of L-Ascorbic Acid: Regioselective and Stereocontrolled 2-C- and 3-C-Allylation via Thermal Claisen Rearrangement

  摘要：

  We report the convenient preparation of 3-O- and 2-O-allylated derivatives of 5,6-O-isopropylidene-L-ascorbic acid (1) with various allyl substituents in high yield and their quantitative thermal Claisen rearrangement to the corresponding 2-C- and 3-C-allylated derivatives with high regio- and stereoselectivity under relatively mild conditions. This reaction will now allow the synthesis of heretofore unknown 3-C-allylated derivatives of L-ascorbic acid in high yield. The high chiral induction at the substituents of the allylic carbon, especially in the case of the 3-O-methyl-2-O-crotyl derivative, is intriguing. This general method of preparation of 2-C- and 3-C-allylated derivatives of ascorbic acid may have important applications in synthetic organic and pharmaceutical chemistry.

  DOI：

  10.1021/jo00091a036
• 作为产物：
  描述：

  5,6-O-isopropylidene-L-ascorbic acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.5h， 生成 5,6-O-Isopropylidene-2-O-allyl-3-O-methyl-L-ascorbic acid
  参考文献：
  名称：

  L-抗坏血酸的化学选择性烷基化

  摘要：

  描述了对制备5-，6-O-异亚丙基-L-抗坏血酸的3-O-烷基和被不同保护的2.3-二-O-烷基衍生物的一般化学选择方法的研究。

  DOI：

  10.1016/0040-4020(95)00959-0

文献信息

• Chemoselective alkylation of L-ascorbic acid
  作者：Mukund G. Kulkarni、Shankar R. Thopate

  DOI：10.1016/0040-4020(95)00959-0

  日期：1996.1

  A study on a general chemoselective method for the preparation of 3-O-alkyl and differentially protected 2.3-di-O-alkyl derivatives of 5,6-O-isopropylidene-L-ascorbic acid is described.

  描述了对制备5-，6-O-异亚丙基-L-抗坏血酸的3-O-烷基和被不同保护的2.3-二-O-烷基衍生物的一般化学选择方法的研究。
• Chemistry of L-Ascorbic Acid: Regioselective and Stereocontrolled 2-C- and 3-C-Allylation via Thermal Claisen Rearrangement
  作者：Kandatege Wimalasena、Mathew P. D. Mahindaratne

  DOI：10.1021/jo00091a036

  日期：1994.6

  We report the convenient preparation of 3-O- and 2-O-allylated derivatives of 5,6-O-isopropylidene-L-ascorbic acid (1) with various allyl substituents in high yield and their quantitative thermal Claisen rearrangement to the corresponding 2-C- and 3-C-allylated derivatives with high regio- and stereoselectivity under relatively mild conditions. This reaction will now allow the synthesis of heretofore unknown 3-C-allylated derivatives of L-ascorbic acid in high yield. The high chiral induction at the substituents of the allylic carbon, especially in the case of the 3-O-methyl-2-O-crotyl derivative, is intriguing. This general method of preparation of 2-C- and 3-C-allylated derivatives of ascorbic acid may have important applications in synthetic organic and pharmaceutical chemistry.