5,6-O-isopropylidene-2-O-(4-bromobenzyl)-L-ascorbic acid | 1453087-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,6-O-isopropylidene-2-O-(4-bromobenzyl)-L-ascorbic acid
• 英文别名: (2R)-4-[(4-bromophenyl)methoxy]-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2H-furan-5-one
• CAS: 1453087-26-7
• 化学式: C₁₆H₁₇BrO₆
• 分子量: 385.211
• InChiKey: FAWCVHQWHLXSKP-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,6-O-isopropylidene-L-ascorbic acid 在 四丁基氟化铵 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 5,6-O-isopropylidene-2-O-(4-bromobenzyl)-L-ascorbic acid
  参考文献：
  名称：

  One-Pot 2-O-Alkylation of l-Ascorbic Acid

  摘要：

  One-pot 2-O-alkylation of L-ascorbic acid involving an in situ 3-O-silylation and desilylation sequence was investigated. Initially the 3-OH group was masked with a t-butyldimethylsilyl (TBDMS) group followed by alkylation of the 2-OH group. Removal of the TBDMS group using 20% sulfuric acid also resulted in hydrolysis of the 5,6-O-isopropylidene to give 2-O-alkyl derivatives of L-ascorbic acid. Selective removal of the 3-O-TBDMS with tetrabutylammonium fluoride (TBAF) gave 5,6-O-isopropylidene-2-O-alkyl derivatives of L-ascorbic acid in good overall yields. Through the application of this protocol, 5,6-O-isopropylidene 2-O-alkyl derivatives of L-ascorbic acid as well as 2-O-alkyl derivatives of L-ascorbic acid may be easily accessed.

  DOI：

  10.1055/s-0033-1338858

文献信息

• One-Pot 2-O-Alkylation of l-Ascorbic Acid
  作者：Shankar Thopate、Rohit Dengale、Mukund Kulkarni

  DOI：10.1055/s-0033-1338858

  日期：——

  One-pot 2-O-alkylation of L-ascorbic acid involving an in situ 3-O-silylation and desilylation sequence was investigated. Initially the 3-OH group was masked with a t-butyldimethylsilyl (TBDMS) group followed by alkylation of the 2-OH group. Removal of the TBDMS group using 20% sulfuric acid also resulted in hydrolysis of the 5,6-O-isopropylidene to give 2-O-alkyl derivatives of L-ascorbic acid. Selective removal of the 3-O-TBDMS with tetrabutylammonium fluoride (TBAF) gave 5,6-O-isopropylidene-2-O-alkyl derivatives of L-ascorbic acid in good overall yields. Through the application of this protocol, 5,6-O-isopropylidene 2-O-alkyl derivatives of L-ascorbic acid as well as 2-O-alkyl derivatives of L-ascorbic acid may be easily accessed.