(2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine hydrochloride | 210115-92-7

• 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: (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine hydrochloride
• 英文别名: (2R,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol hydrochloride；(2R,3R,4R,5R)-2,5-bis(hydroxymethyl)-3,4-dihydroxypyrrolidine hydrochloride；2,5-Dideoxy-2,5-imino-D-mannitol hcl；(2R,3R,4R,5R)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol;hydrochloride
• CAS: 210115-92-7
• 化学式: C₆H₁₃NO₄*ClH
• 分子量: 199.634
• InChiKey: ASOISZHLRDHELT-MVNLRXSJSA-N

物化性质

• 熔点：
  >150 °C (decomp)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.54
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93
• 氢给体数：
  6
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine hydrochloride 在 DOWEX 50W*8 作用下， 以11 mg的产率得到Alpha-葡萄糖苷酶
  参考文献：
  名称：

  1,3-Oxazine as a chiral building block used in the total synthesis of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)-dihydroxypyrrolidine

  摘要：

  Concise and stereocontrolled syntheses of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)dihydroxypyrrolidine [(+)-DMDP] were achieved via a diastereomerically enriched oxazine intermediate. The key strategies include the use of 1,3-oxazine as a chiral building block and diastereoselective nucleophilic addition to an aldehyde. Starting from readily available (R)-methyl 2-benzamido-3-((tertbutyldimethylsilyl)oxy)propanoate, (+)-1-deoxynojirimycin was synthesized in 11 steps and 26.2% overall yield while (+)-DMDP was synthesized in 11 steps and 27.1% overall yield, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.05.008
• 作为产物：
  描述：

  (2R,3R,4R,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-(hydroxymethyl)pyrrolidin-3-ol 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (2R,3R,4R,5R)-2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine hydrochloride
  参考文献：
  名称：

  1,3-Oxazine as a chiral building block used in the total synthesis of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)-dihydroxypyrrolidine

  摘要：

  Concise and stereocontrolled syntheses of (+)-1-deoxynojirimycin and (2R,5R)-dihydroxymethyl-(3R,4R)dihydroxypyrrolidine [(+)-DMDP] were achieved via a diastereomerically enriched oxazine intermediate. The key strategies include the use of 1,3-oxazine as a chiral building block and diastereoselective nucleophilic addition to an aldehyde. Starting from readily available (R)-methyl 2-benzamido-3-((tertbutyldimethylsilyl)oxy)propanoate, (+)-1-deoxynojirimycin was synthesized in 11 steps and 26.2% overall yield while (+)-DMDP was synthesized in 11 steps and 27.1% overall yield, respectively. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.05.008

文献信息

• Nucleophilic Additions to Cyclic Nitrones en Route to Iminocyclitols – Total Syntheses of DMDP, 6-deoxy-DMDP, DAB-1, CYB-3, Nectrisine, and Radicamine B
  作者：Pedro Merino、Ignacio Delso、Tomás Tejero、Francesca Cardona、Marco Marradi、Enrico Faggi、Camilla Parmeggiani、Andrea Goti

  DOI：10.1002/ejoc.200800098

  日期：2008.6

  with total diastereoselectivity and in quantitative yield, with no purification being necessary. By this strategy, 2-(hydroxymethyl)-, 2-(aminomethyl)-, and 2-aryl-substituted polyhydroxylated pyrrolidines have been prepared with abundant configurational diversity. The use of appropriate substrates and reagents allowed for approaches to DMDP, 6-deoxy-DMDP, DAB-1, CYB-3, nectrisine and radicamine B. Several

  对衍生自 L-苹果酸和 D-阿拉伯糖的环状硝酮的高度非对映选择性亲核加成已用于构建对映异构纯的多羟基化吡咯烷。所采用的合成策略基于涉及羟胺/硝酮对的氧化/还原协议，并演示了试剂和底物衍生立体控制的使用。在大多数情况下，反应以完全非对映选择性和定量收率发生，无需纯化。通过这种策略，已经制备了具有丰富构型多样性的 2-(羟甲基)-、2-(氨基甲基)-和 2-芳基取代的多羟基吡咯烷。适当的底物和试剂的使用允许接近 DMDP、6-脱氧-DMDP、DAB-1、CYB-3、油桃和雷卡胺 B。