1,4-二脱氧-1,4-亚氨基-L-核糖醇盐酸盐 | 117770-01-1

• 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: 1,4-二脱氧-1,4-亚氨基-L-核糖醇盐酸盐
• 英文名称: (2S,3S,4R)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine hydrochloride
• 英文别名: (2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol hydrochloride；1,4-dideoxy-1,4-L-iminoribitol hydrochloride；1,4-dideoxy-1,4-imino-L-ribitol hydrochloride；(2S,3S,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol;hydrochloride
• CAS: 117770-01-1
• 化学式: C₅H₁₁NO₃*ClH
• 分子量: 169.608
• InChiKey: PZGVJCJRMKIVLJ-VEGRVEBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.91
• 重原子数：
  10
• 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：
  5
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4-戊二烯酸 在 palladium on activated charcoal 、 四氧化锇 N-甲基吗啉 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 amberlyst-15 、 氢气 、 碳酸氢钠 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 33.25h， 生成 1,4-二脱氧-1,4-亚氨基-L-核糖醇盐酸盐
  参考文献：
  名称：

  Straightforward Synthesis of Pyrrolidine Glycosidase Inhibitors via Asymmetric Hetero-Diels-Alder Reaction

  摘要：

  通过不对称杂狄尔斯-阿尔德反应从戊二烯酸 4 获得，然后进行简单的化学转化，恶嗪羧酸酯 8 进行碱催化重排，得到受保护的三羟基脯氨酸 9。使用各种还原条件，有效的糖苷酶抑制剂 1，获得4-二脱氧-1,4-亚氨基-D-来木糖醇D-1和1,4-二脱氧-1,4-亚氨基-L-核糖醇L-2。

  DOI：

  10.1055/s-1997-5794

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。
• Heterocyclic compounds for inhibiting virus
  申请人：Monsanto Company

  公开号：EP0322395A1

  公开（公告）日：1989-06-28

  Various heterocyclic compounds, namely (a) the N-methyl derivative of di(hydroxymethyl)-dihydroxy­pyrrolidine, (b) 1,4-dideoxy-1,4-imino-L-arabinitol, (c) 1,4-dideoxy-1,4-imino-L-ribitol, (d) 1,4-dideoxy-1,4-imino-D-ribitol, (e) 1,4-dideoxy-1,4-imino-(N-methyl)-L-arabinitol, (f) 1,4-dideoxy-1,4-imino-(N-methyl)-D-ribitol, (g) 1,4-dideoxy-1,4-benzylimino-L-ribitol, (h) 1,4-dideoxy-1,4-imino-D-talitol, (i) the N-methyl derivative of deoxymannojirimycin, (j) 1,5-dideoxy-1,5-imino-L-fuconolactam, (k) 1,5-dideoxy-1,5-imino-(N-methyl)-L-fucitol, (l) 1,5-dideoxy-1,5-imino-(N-ω-methyl caproate)-L-fucitol, and their pharmaceutically acceptable salt derivatives are useful as inhibiting agents of human immunodeficiency virus. Compounds (a), (e), (j), (k) and (l) are new.

  各种杂环化合物，即 (a) 二（羟甲基）-二羟基吡咯烷的 N-甲基衍生物、 (b) 1,4-二脱氧-1,4-亚氨基-L-阿拉伯糖醇、 (c) 1,4-二脱氧-1,4-亚氨基-L-核糖醇、 (d) 1,4-二脱氧-1,4-亚氨基-D-核糖醇、 (e) 1,4-二脱氧-1,4-亚氨基-(N-甲基)-L-阿拉伯糖醇、 (f) 1,4-二脱氧-1,4-亚氨基-(N-甲基)-D-核糖醇、 (g) 1,4-二脱氧-1,4-苄基亚氨基-L-核糖醇、 (h) 1,4-二脱氧-1,4-亚氨基-D-谷糖醇、 (i) 脱氧曼尻霉素的 N-甲基衍生物、 (j) 1,5-二脱氧-1,5-亚氨基-L-岩藻内酰胺、 (k) 1,5-二脱氧-1,5-亚氨基-(N-甲基)-L-岩藻糖醇、 (l) 1,5-二脱氧-1,5-亚氨基-(N-ω-甲基己酸酯)-L-岩藻糖醇、 及其药学上可接受的盐衍生物可用作人类免疫缺陷病毒的抑制剂。化合物(a)、(e)、(j)、(k)和(l)是新化合物。
• Chiral synthesis of both enantiomers of 1,4-dideoxy-1,4-immolyxitol and 1,4-dideoxy-1,4-iminoribitol
  作者：Seiichi Takano、Minoru Moriya、Kunio Ogasawara

  DOI：10.1016/s0957-4166(00)80499-1

  日期：1992.6

  Reaction of 2,3-dibromopropionyl chloride with 4-methoxyphenol and (S)-1-methlbenzylamine yielded a 4:5 mixture of readily separable diastereomeric aziridine esters in an excellent yield. Both diastereomers, upon heating with vinylene carbonate, furnished four readily separable diastereomeric pyrrolidine esters, respectively, which were transformed into both enantiomers of 1,4-dideoxy-1,4-iminolyxitol and 1,4-dideoxy-1,4-iminoribitol.
• A facile synthesis of 1,4-dideoxy-1,4-imino-l-ribitol (LRB) and (−)-8a-epi-swainsonine from d-glutamic acid
  作者：Xiao-Ling Wang、Wen-Feng Huang、Xin-Sheng Lei、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1016/j.tet.2011.04.075

  日期：2011.7

  A facile synthesis of (-)-8a-epi-swainsonine 2 and 1,4-dideoxy-1,4-imino-L-ribitol (LRB) 4 has been achieved by using the versatile building block 3, which was available from cheap D-glutamic acid. The new forming stereogenic center in synthesis of 2 was constructed by highly selective reduction of the ketone 13 with Li(t-BuO)(3)AlH in THF (dr=95:5). (C) 2011 Elsevier Ltd. All rights reserved.
• Ikota, Nobuo; Hanaki, Akira, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 4, p. 1087 - 1089
  作者：Ikota, Nobuo、Hanaki, Akira

  DOI：——

  日期：——