2-O-isopropyl-L-ascorbic acid | 1453087-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-O-isopropyl-L-ascorbic acid
• 英文别名: (2R)-2-[(1S)-1,2-dihydroxyethyl]-3-hydroxy-4-propan-2-yloxy-2H-furan-5-one
• CAS: 1453087-20-1
• 化学式: C₉H₁₄O₆
• 分子量: 218.207
• InChiKey: SKRWFAWKMHSLDX-CAHLUQPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,6-O-isopropylidene-L-ascorbic acid 在 硫酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 2-O-isopropyl-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

• ADAM INHIBITOR
  申请人：Shiseido Company, Ltd.

  公开号：EP2123272A1

  公开（公告）日：2009-11-25

  Disclosed is an ADAM inhibitor which enables to prevent or improve conditions caused by increase in ADAM activity. Specifically disclosed is an ascorbic acid derivative represented by the general formula (1) below or a salt thereof. [chemical formula 1] (1), wherein R represents a linear or branched alkyl group having 1 to 22 carbon atoms.

  本发明公开了一种ADAM抑制剂，它能够预防或改善因ADAM活性增加而引起的病症。具体公开了由下式（1）通式代表的抗坏血酸衍生物或其盐。[化学式 1] (1)，其中 R 代表具有 1 至 22 个碳原子的直链或支链烷基。