1,4-dideoxy-1,4-imino-D-allitol hydrochloride | 117770-16-8

• 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-1,4-imino-D-allitol hydrochloride
• 英文别名: (2R,3R,4S)-2-[(1S)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol;hydrochloride
• CAS: 117770-16-8
• 化学式: C₆H₁₃NO₄*ClH
• 分子量: 199.634
• InChiKey: IFRNNJQXHHLGKS-NQZVPSPJSA-N

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

• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-D-gulose oxime 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 40.5h， 生成 1,4-dideoxy-1,4-imino-D-allitol hydrochloride
  参考文献：
  名称：

  Buchanan, J. Grant; Lumbard, Keith W.; Sturgeon, Robert J., Journal of the Chemical Society. Perkin transactions I, 1990, p. 699 - 706

  摘要：

  DOI：

文献信息

• A divergent, short, and stereoselective approach to pyrrolidine iminosugars: synthesis of 1,4-dideoxy-1,4-imino-derivatives of d-allitol, d-ribitol, ethyl-erythritol, and (−)-2,3-trans-3-4-cis-dihydroxyproline
  作者：Sahadev S. Chirke、Anugula Rajender、Jerripothula K. Lakshmi、Batchu Venkateswara Rao

  DOI：10.1016/j.tetlet.2015.01.115

  日期：2015.3

  A highly stereoselective addition of Grignard reagent on lactamine for the synthesis of 1,4-dideoxy-1,4-imino-derivatives of d-allitol, d-ribitol, ethyl-erythritol, and (−)-2,3-trans-3-4-cis-dihydroxyproline has been described from commercially available d-ribose as a starting material.

  在乳糖胺上进行格利雅试剂的高度立体选择性加成反应，以合成d-烯醇，d-核糖醇，乙基-赤藓糖醇和（-）-2,3-反式-已经从可商购的d-核糖描述了3--4-顺-二羟基脯氨酸作为起始原料。
• Enantioselective synthesis of hydroxylated pyrrolidines via Sharpless epoxidation and olefin metathesis
  作者：Caterina Murruzzu、Antoni Riera

  DOI：10.1016/j.tetasy.2006.12.023

  日期：2007.1

  The enantioselective synthesis of polyhydroxylated pyrrolidines from enantiomerically pure 2,3-epoxy-pent-4-en-1-ol 5 is described herein. The epoxy alcohol, readily available in any configuration by Sharpless epoxidation, was submitted to regioselective C-3 ring-opening with allyl amine, Boc-protection and ring-closing metathesis to yield dehydropyrrole derivative 7. From this key intermediate, 1

  本文描述了由对映体纯的2，3-环氧-戊-4-烯-1-醇5对映体选择性合成多羟基化的吡咯烷。可以通过Sharpless环氧化容易地以任何构型获得的环氧醇，经过烯丙基胺的区域选择性C-3开环，Boc保护和开环易位，得到脱氢吡咯衍生物7。从该关键中间体中，高浓度地制备了1,4-二脱氧-1,4-亚氨基-d-核糖醇（+）- 3和1,4-二脱氧-1,4-亚氨基-d-烯丙醇（+）- 4。产量。这些化合物的对映异构体可以从具有相反构型的环氧醇开始以相同的顺序获得。
• Efficient stereodivergent synthesis of 1,4-dideoxy-1,4-iminohexitols from an (S)-glyceraldimine
  作者：Ramón Badorrey、Carlos Cativiela、Marı́a D. Dı́az-de-Villegas、Roberto Dı́ez、José A. Gálvez

  DOI：10.1016/j.tetlet.2003.11.053

  日期：2004.1

  A stereodivergent synthesis of 1,4-dideoxy-1,4-imino-d-mannitol I and d-allitol III from an (S)-glyceraldimine, which is easily prepared from d-mannitol, has been achieved with overall yields of 62% and 49%, respectively. The synthesis is based on the addition of vinylmagnesium bromide to N-benzylimine 1, derived from readily available (R)-2,3-O-isopropylideneglyceraldehyde, followed by N-allylation

  由（S）-丙二胺可容易地由d-甘露糖醇制备1,4-二脱氧-1,4-亚氨基-d-甘露糖醇I和d-阿糖醇III的立体发散性合成，总收率为62 ％和49％。合成是基于除了乙烯基溴化镁于Ñ -benzylimine 1，从容易获得的（派生- [R）-2,3- Ô -isopropylideneglyceraldehyde，随后Ñ -allylation或Ñ -acryloylation，闭环复分解和不对称二羟基化。
• 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。
• Stereoselective synthesis of 1,4-dideoxy-1,4-imino-d-allitol and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline
  作者：A Madhan、B Venkateswara Rao

  DOI：10.1016/s0040-4039(03)01366-2

  日期：2003.7

  A stereoselective synthesis of 1,4-dideoxy-1,4-imino-D-allitol 1 and formal synthesis of (2S,3R,4S)-3,4-dihydroxyproline was achieved via the addition of vinylmagnesium bromide to the benzylimine derived from (R)-2,3-O-isopropylidene glyceraldehyde followed by N-allylation, ring-closing metathesis (RCM), and dihydroxylation. (C) 2003 Elsevier Ltd. All rights reserved.