2,3-bis-O-allyl-5,6-O-isopropylidene-L-ascorbic acid | 95628-60-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-bis-O-allyl-5,6-O-isopropylidene-L-ascorbic acid
• 英文别名: 2,3-di-O-allyl-5,6-O-isopropylidene-L-ascorbic acid；5,6-O-isopropylidene-2,3-di-O-allyl-L-ascorbic acid；5,6-O-Isopropylidene-2,3-O-diallyl-L-ascorbic acid；(2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-bis(prop-2-enoxy)-2H-furan-5-one
• CAS: 95628-60-7
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: NUEFTURFZQMGGL-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  2,3-bis-O-allyl-5,6-O-isopropylidene-L-ascorbic acid 在 sodium tetrahydroborate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.58h， 生成 5,6-O-isopropylidene-2-O-(1-prop-2-enyl)-2-(1-prop-2-enyl)-L-gulono-γ-lactone
  参考文献：
  名称：

  从抗坏血酸到C2和C3取代的Gulono-γ-内酯衍生物的简便方法

  摘要：

  描述了一种方便的方法，该方法从1-抗坏血酸开始获得未知的手性C2-和C3官能化的aldono-1,4-内酯衍生物，这对合成各种用于结构活性研究的药理活性剂具有价值的方法。该方法的实用性通过合成一系列的5，6 - O-异亚丙基-2-烯丙基-3-酮基-1-半乳糖-γ-内酯和5，6 - O-异亚丙基-3-烯丙基-来证明。 2-酮升使用相应的3-的热克莱森重排-galactono-γ内酯衍生物ø -和2- ö 5,6-的烯丙基衍生物ö异亚丙基升-抗坏血酸，然后立体定向还原为相应的醇。合成步骤被证明是有效的和对映体特异性的，并且它们以高收率进行。

  DOI：

  10.1021/jo0508550
• 作为产物：
  描述：

  5,6-O-isopropylidene-L-ascorbic acid 在 potassium carbonate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 6.67h， 生成 2,3-bis-O-allyl-5,6-O-isopropylidene-L-ascorbic acid
  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

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。
• l-Ascorbic acid in organic synthesis: DBU-catalysed one-pot synthesis of tetramic acid derivatives from 5,6-O-isopropylidene ascorbic acid
  作者：Biswajit K. Singh、Shyam S. Verma、Namrata Dwivedi、Rama P. Tripathi

  DOI：10.1016/j.tetlet.2006.01.098

  日期：2006.3

  Reaction of 5,6-O-isopropylidene-2,3-bis-O-alkyl ascorbic acid with different amines in the presence of DBU at ambient temperature resulted in the formation of 3,4-bis-O-alkyl-l-alkyl-5-(2-hydroxy ethyl)-5-hydroxy-1,5-dihydropyrrol-2-ones in moderate yields. (c) 2006 Elsevier Ltd. All rights reserved.
• Diastereoselective transannular [2+2] photocycloaddition of ascorbic acid derivatives
  作者：Sébastien Redon、Olivier Piva

  DOI：10.1016/j.tetlet.2005.11.102

  日期：2006.1

  Ring-closing metathesis of bis-O,O-alkenyl ascorbic acid derivatives affords cyclic ethers in good yields which can be further converted by irradiation at 254 nm into new polyoxacyclic structures according to a diastereoselective transannular [2+2] photocycloaddition. (c) 2005 Elsevier Ltd. All rights reserved.
• Regio- and Chemoselective Alkylation of <scp>l</scp>-Ascorbic Acid under Mitsunobu Conditions
  作者：Hasan Tahir、Ole Hindsgaul

  DOI：10.1021/jo990606+

  日期：2000.2.1
• 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.