(2R,3S,4S)-2-羟甲基四氢吡咯-3,4-二醇 | 97058-12-3

• 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: (2R,3S,4S)-2-羟甲基四氢吡咯-3,4-二醇
• 英文名称: 1,4-dideoxy-1,4-imino-D-xylitol
• 英文别名: (2r,3s,4s)-2-(Hydroxymethyl)pyrrolidine-3,4-diol
• CAS: 97058-12-3
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: OQEBIHBLFRADNM-WISUUJSJSA-N

物化性质

• 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：

  (2R,3S,4S)-2-羟甲基四氢吡咯-3,4-二醇 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 1'-((1,4-dideoxy-1,4-imino-D-xylitol)-4-N-ammonium)-1'-deoxy-L-erythritol-3'-sulfate
  参考文献：
  名称：

  Synthesis of 1,4-anhydro-D-xylitol heteroanalogues of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors

  摘要：

  本文介绍了两个1,4-脱水-D-木糖醇杂环类似物（8和9），它们含有一个硫或氮原子的环，是天然存在的亚磺酸盐离子salacinol（3）的合成方法。Salacinol（3）是Sri Lanka和India传统用于2型糖尿病治疗的Salacia reticulata水提取物中的有效成分之一。合成策略依赖于硫或氮类似物1,4-脱水-D-木糖醇的亲核攻击2,4-O-苯甲酰亚甲基-L-赤藓醇-1,3-环状硫酸酯的最不妨碍碳。亚磺酸盐离子8抑制了大麦α-淀粉酶（AMY1）和猪胰腺α-淀粉酶（PPA），其K i 值分别为109 ± 11和55 ± 5 µM。相比之下，铵离子9对AMY1或PPA均未显示出显著抑制作用。化合物8和9也未显示出对葡萄糖淀粉酶的显著抑制作用。关键词：糖苷酶抑制剂，salacinol类似物，脱水-D-木糖醇杂环类似物，酶抑制。

  DOI：

  10.1139/v02-078
• 作为产物：
  描述：

  (6S,7S,7aR)-6,7-dihydroxy-tetrahydro-pyrrolo[1,2-c]oxazol-3-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (2R,3S,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

• 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。
• An efficient synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol and 1,4-dideoxy-1,4-imino-d- and l-xylitol from chiral aziridines
  作者：Hwan Geun Choi、Dong-Sik Park、Won Koo Lee、Taebo Sim

  DOI：10.1016/j.tetlet.2013.08.040

  日期：2013.10

  highly efficient method for the synthesis of 1,4-dideoxy-1,4-imino-d- and l-arabinitol (d-AB1, 1 and l-AB1, 3) and 1,4-dideoxy-1,4-imino-d- and l-xylitol (d-DIX, 2 and l-DIX, 4) starting from commercially available chiral aziridines was developed. The general strategy employs a sequence involving two-carbon homologation, dihydroxylation, and regioselective aziridine ring opening/intramolecular five-membered

  为1,4-二去氧-1,4-亚氨基的合成高效方法d -和升-arabinitol（d -AB1，1个升-AB1，3）和1,4-二脱氧-1,4-亚氨基d-和l-木糖醇（d -DIX，2和l -DIX，4）从商业上可获得的手性氮丙啶开始开发。一般策略采用的序列涉及两碳同源，二羟基化和区域选择性氮丙啶开环/分子内五元亚氨基糖环的形成。重结晶以生成纯的非对映异构体的简便方法使该路线更适合大规模合成。
• Identification of the 2-hydroxymethyl-3,4-dihydroxypyrrolidine (or 1,4-dideoxy-1,4-iminopentitol) from and from as the (2R, 3R, 4S)-isomer by the synthesis of its enantiomer.
  作者：D.Wyn C. Jones、Robert J. Nash、E.Arthur Bell、J.Michael Williams

  DOI：10.1016/s0040-4039(00)98635-0

  日期：1985.1
• Total Synthesis Without Protecting Groups: Pyrrolidines and Cyclic Carbamates
  作者：Emma M. Dangerfield、Mattie S. M. Timmer、Bridget L. Stocker

  DOI：10.1021/ol802484y

  日期：2009.2.5

  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.
• Synthesis of 1,4-anhydro-<scp>D</scp>-xylitol heteroanalogues of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors
  作者：Ahmad Ghavami、Blair D Johnston、Matthew D Maddess、Sarah M Chinapoo、Morten T Jensen、Birte Svensson、B Mario Pinto

  DOI：10.1139/v02-078

  日期：2002.8.1

  The syntheses of two 1,4-anhydro-D-xylitol heteroanalogues (8 and 9) of the naturally occurring sulfonium ion, salacinol (3), containing a sulfur or nitrogen atom in the ring are described. Salacinol (3) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of Type 2 diabetes. The synthetic strategy relies on the nucleophilic attack of sulfur or nitrogen analogues of 1,4-anhydro-D-xylitol at the least-hindered carbon of 2,4-O-benzylidene-L-erythritol-1,3-cyclic sulfate. The sulfonium ion 8 inhibited barley-α-amylase (AMY1) and porcine pancreatic-α-amylase (PPA), with K_i values of 109 ± 11 and 55 ± 5 µM, respectively. In contrast, the ammonium ion 9 showed no significant inhibition of either AMY1 or PPA. Compounds 8 and 9 also showed no significant inhibition of glucoamylase.Key Words: glycosidase inhibitors, salacinol analogues, anhydro-D-xylitol heteroanalogues, enzyme inhibition.

  本文介绍了两个1,4-脱水-D-木糖醇杂环类似物（8和9），它们含有一个硫或氮原子的环，是天然存在的亚磺酸盐离子salacinol（3）的合成方法。Salacinol（3）是Sri Lanka和India传统用于2型糖尿病治疗的Salacia reticulata水提取物中的有效成分之一。合成策略依赖于硫或氮类似物1,4-脱水-D-木糖醇的亲核攻击2,4-O-苯甲酰亚甲基-L-赤藓醇-1,3-环状硫酸酯的最不妨碍碳。亚磺酸盐离子8抑制了大麦α-淀粉酶（AMY1）和猪胰腺α-淀粉酶（PPA），其K i 值分别为109 ± 11和55 ± 5 µM。相比之下，铵离子9对AMY1或PPA均未显示出显著抑制作用。化合物8和9也未显示出对葡萄糖淀粉酶的显著抑制作用。关键词：糖苷酶抑制剂，salacinol类似物，脱水-D-木糖醇杂环类似物，酶抑制。