(2S,3R,4S)-2-羟甲基四氢吡咯-3,4-二醇 | 129568-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (2S,3R,4S)-2-羟甲基四氢吡咯-3,4-二醇
• 英文名称: (2S,3R,4S)-2-hydroxymethyl-pyrrolidine-3,4-diol
• 英文别名: 1,4-dideoxy-1,4-imino-L-lyxitol；L-iminolyxitol；(2S,3R,4S)-2-(hydroxymethyl)pyrrolidine-3,4-diol；cis-D-Dihydroxyprolinol
• CAS: 129568-47-4
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: OQEBIHBLFRADNM-VAYJURFESA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  319.1±37.0 °C(Predicted)
• 密度：
  1.368±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 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

• 作为反应物：
  描述：

  (2S,3R,4S)-2-羟甲基四氢吡咯-3,4-二醇 在 盐酸 作用下， 以 水 为溶剂， 以30 mg的产率得到1,4-dideoxy-1,4-imino-L-lyxitol hydrochloride
  参考文献：
  名称：

  Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-d-lyxitol [a potent competitive inhibitor of α-d-galactosidase] and of 1,4-dideoxy-1,4-imino-l-lyxitol [a weak competitive inhibitor of α-d-galactosidase] inhibit naringinase, an α-l-rhamnosidase competitively

  摘要：

  Benzhydryl protection by diphenyldiazomethane of an alcohol in enantiomeric base-sensitive ribonolactones allows short efficient syntheses of 1,4-dideoxy-1,4-imino-D-lyxitol (DIL) and of 1,4-dideoxy-1,4-imino-L-lyxitol (LIL). DIL showed potent [K-i = 0.13 mu M]-and LIL showed weak [K-i = 113 mu M]-competitive inhibition of alpha-D-galactosidase. Both enantiomers N-benzyl-DIL [K-i = 64 mu M] and N-benzyl-LIL [K-i = 13 mu M] were moderate competitive inhibitors of naringinase, an alpha-L-rhamnosidase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.004
• 作为产物：
  描述：

  (6S,7R,7aS)-6,7-dihydroxy-tetrahydropyrrolo[1,2-c]oxazol-3-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (2S,3R,4S)-2-羟甲基四氢吡咯-3,4-二醇
  参考文献：
  名称：

  Total Synthesis Without Protecting Groups: Pyrrolidines and Cyclic Carbamates

  摘要：

  A protecting group free synthesis of 2,3-cis substituted hydroxypyrrolidines is reported. Two novel reaction methodologies allow for the stereoselective formation of cyclic carbamates from olefinic amines, and the formation of primary amines via a Vasella/reductive amination reaction, both performed in aqueous media.

  DOI：

  10.1021/ol802484y

文献信息

• An <i>in vitro–in vivo</i> sequential cascade for the synthesis of iminosugars from aldoses
  作者：Justyna Kuska、Freya Taday、Kathryn Yeow、James Ryan、Elaine O'Reilly

  DOI：10.1039/d1cy00698c

  日期：——

  Here, we report a chemoenzymatic approach for the preparation of a small panel of biologically important iminosugars from readily available aldoses, employing a transaminase in combination with Gluconobacter oxydans whole cells.

  在这里，我们报告了一种化学酶法，用于从易于获得的醛糖制备一组具有重要生物学意义的亚硝基糖，方法是使用转氨酶与氧化葡萄糖菌全细胞结合。

• The Efficient, Enantioselective Synthesis of Aza Sugars from Amino Acids. 1. The Polyhydroxylated Pyrrolidines
  作者：Yifang Huang、David R. Dalton、Patrick J. Carroll

  DOI：10.1021/jo962028s

  日期：1997.1.1

  (+)-serine or (-)-serine, as appropriate, convenient, high-yield, enantioselective synthesis of all eight stereoisomeric 2-hydroxymethyl-3,4-dihydroxypyrrolidines (the enantiomeric pairs of iminoribitol, -arabinitol, -xylitol, and -lyxitol) can be effected. The absolute configuration of the starting amino acid defines the set of azasugars produced.

  从（+）-丝氨酸或（-）-丝氨酸开始，视情况，方便，高产，对映选择性合成所有八个立体异构体2-羟甲基-3,4-二羟基吡咯烷酮（亚氨基核糖醇，-阿拉伯糖醇，-木糖醇的对映体对） ，和-lyxitol）。起始氨基酸的绝对构型定义了所产生的氮杂糖的集合。
• Wehner, Volkmar; Jaeger, Volker, Angewandte Chemie, 1990, vol. 102, # 10, p. 1180 - 1182
  作者：Wehner, Volkmar、Jaeger, Volker

  DOI：——

  日期：——
• Stereoselective Synthesis of 1,4-Dideoxy-1,4-imino-L-lyxitol and 1,5-Dideoxy-1,5-imino-D-ribitol
  作者：Ki Hun Park、Ki Chang Jang、Ill-Yun Jeong、Min Suk Yang、Sang Uk Choi

  DOI：10.3987/com-99-8832

  日期：——
• DUREAULT, ANNIE;GRECK, CHRISTINE;DEPEZAY, JEAN-CLAUDE, J. CARBOHYDR. CHEM., 9,(1990) N, C. 121-123
  作者：DUREAULT, ANNIE、GRECK, CHRISTINE、DEPEZAY, JEAN-CLAUDE

  DOI：——

  日期：——