1,4-Dideoxy-1,4-imino-L-allitol Hydrochloride | 129247-80-9

• 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-L-allitol Hydrochloride
• 英文别名: (2S,3S,4R)-2-[(1R)-1,2-dihydroxyethyl]pyrrolidine-3,4-diol;hydrochloride
• CAS: 129247-80-9
• 化学式: C₆H₁₃NO₄*ClH
• 分子量: 199.634
• InChiKey: IFRNNJQXHHLGKS-OLALXQGDSA-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：

  2,6-dibromo-2,6-dideoxy-D-mannitol 在 ammonium hydroxide 作用下， 反应 2.0h， 以51%的产率得到1,4-Dideoxy-1,4-imino-L-allitol Hydrochloride
  参考文献：
  名称：

  Lundt; Madsen, Synthesis, 1993, # 7, p. 714 - 720

  摘要：

  DOI：

文献信息

• Stereo-controlled approach to pyrrolidine iminosugar C-glycosides and 1,4-dideoxy-1,4-imino-l-allitol using a d-mannose-derived cyclic nitrone
  作者：Omprakash P. Bande、Vrushali H. Jadhav、Vedavati G. Puranik、Dilip D. Dhavale、Marco Lombardo

  DOI：10.1016/j.tetlet.2009.09.139

  日期：2009.12

  Intramolecular N-alkylation of 2,3-O-isopropylidene-5-O-methanesulfonyl-6-O-t-butyldimethylsilyl-d-mannofuranose-oxime 7 afforded a five-membered cyclic nitrone 9, which on N–O bond reductive cleavage followed by deprotection of –OTBS and acetonide functionalities gave 1,4-dideoxy-1,4-imino-l-allitol (DIA) 3. Addition of allylmagnesium chloride to nitrone 9 afforded α-allylated product 10a in high

  分子内N-烷基化的2,3- ø异亚丙基-5- ö甲磺酰基- 6- ø -吨-butyldimethylsilyl- d -mannofuranose肟7，得到的五元环状硝酮9，其上ñ - ö键还原裂解然后对–OTBS和丙酮化物进行脱保护，得到1,4-二脱氧-1,4-亚氨基-1-烯丙醇（DIA）3。将烯丙基氯化镁添加到硝酮9中可得到高非对映选择性的α-烯丙基化产物10a，从而易于进入N除去保护基后，用-羟基-C1-α-烯丙基取代的吡咯烷亚氨基糖4a，而在10a中进行N - O键还原裂解，得到C1-α-烯丙基-吡咯烷亚氨基糖4b。
• Novel glycosidase inhibitors
  申请人：MONSANTO COMPANY

  公开号：EP0375651A1

  公开（公告）日：1990-06-27

  The specificity of glycosidase inhibitory activity of the novel 1,4-dideoxy-1,4-imino-L-allitol (I) is substantially changed by substituting the ring nitrogen with an alkyl or benzyl substituent.

  通过用烷基或苄基取代环氮，新型 1,4-二脱氧-1,4-亚氨基-L-谷糖醇（I）的糖苷酶抑制活性的特异性发生了很大变化。
• Buchanan, J. Grant; Lumbard, Keith W.; Sturgeon, Robert J., Journal of the Chemical Society. Perkin transactions I, 1990, p. 699 - 706
  作者：Buchanan, J. Grant、Lumbard, Keith W.、Sturgeon, Robert J.、Thompson, Deryk K.

  DOI：——

  日期：——
• Asymmetric syntheses of polysubstituted homoprolines and homoprolinols
  作者：Kristína Csatayová、Stephen G. Davies、Aude L.A. Figuccia、Ai M. Fletcher、J. Gair Ford、James A. Lee、Paul M. Roberts、Benjamin G. Saward、Haewon Song、James E. Thomson

  DOI：10.1016/j.tet.2015.10.005

  日期：2015.12

  Complementary protocols for the diastereoselective syn- and anti-dihydroxylations of enantiopure dihydropyrrole scaffolds were used as the key steps in the asymmetric syntheses of several polysubstituted homoprolines and homoprolinols. The requisite dihydropyrroles were prepared in three steps from commercially available sorbic acid via either hydroamination or aminohydroxylation of the corresponding tert-butyl ester, followed by ring-closing metathesis. Subsequent olefinic oxidation and deprotection gave access to the corresponding enantiopure homoprolines [(2S,3S,4R)-dihydroxyhomoproline, (2S,3R,4R)-dihydroxyhomoproline and (S,S,S)-3-amino-4-hydroxy-homoproline], enantiopure alpha-hydroxy-homoprolines [3,6-dideoxy-3,6-imino-D-allonic acid and 3,6-dideoxy-3,6-imino-D-gulonic acid] and enantiopure homoprolinols [1,4-dideoxy-1,4-imino-L-allitol and (S,S,S)-3-amino-4-hydroxyhomoprolinol] as single diastereoisomers in good overall yields. (C) 2015 Elsevier Ltd. All rights reserved.
• US4894388A
  申请人：——

  公开号：US4894388A

  公开（公告）日：1990-01-16