1,4-dideoxy-2-C-hydroxymethyl-1,4-imino-D-threitol | 1241760-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1,4-dideoxy-2-C-hydroxymethyl-1,4-imino-D-threitol
• 英文别名: isoDAB；(3S,4R)-3-(hydroxymethyl)pyrrolidine-3,4-diol
• CAS: 1241760-33-7
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: VWMSLTGKBPRHSC-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-C-azidomethyl-2,3-O-isopropylidene-L-erythrose 在 palladium 10% on activated carbon 氢气 、 溶剂黄146 、 氨 作用下， 以 水 为溶剂， 反应 24.0h， 以71%的产率得到1,4-dideoxy-2-C-hydroxymethyl-1,4-imino-D-threitol
  参考文献：
  名称：

  [EN] NOVEL IMINOSUGAR THERAPEUTICS
  [FR] NOUVEAUX AGENTS THÉRAPEUTIQUES IMINOSUCRES

  摘要：

  公开号：

  WO2011095772A3

文献信息

• Cystic fibrosis and diabetes: isoLAB and isoDAB, enantiomeric carbon-branched pyrrolidine iminosugars
  作者：Daniel Best、Sarah F. Jenkinson、A. Waldo Saville、Dominic S. Alonzi、Mark R. Wormald、Terry D. Butters、Caroline Norez、Frederic Becq、Yves Blériot、Isao Adachi、Atsushi Kato、George W.J. Fleet

  DOI：10.1016/j.tetlet.2010.05.131

  日期：2010.8

  Acetonides are the only protecting groups used in the syntheses of isoDAB from D-ribose and of isoLAB from D-tagatose. isoDAB is a potent and highly specific competitive a-glucosidase inhibitor (for rice alpha-glucosidase, K(i) = 4 mu M for isoDAB compared to K(i) 14 mu M for DAB). isoDAB is not an whereas DAB is a potent inhibitor of glycogen phosphorylase. This is the first example of any potent inhibition of glycosidases by a carbon-branched iminosugar pyrrolidine. Although isoLAB shows no inhibition of any glycosidase, preliminary experiments suggest that isoLAB partially rescues the defective F508del-CFTR function and so may have a role in the study of cystic fibrosis. (C) 2010 Elsevier Ltd. All rights reserved.