(2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis(1-tert-butoxycarbonyl)-aziridine | 156856-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis(1-tert-butoxycarbonyl)-aziridine
• 英文别名: (2S,2'S)-((1R,2R)-1,2-dibenzyloxy-ethan-diyl)bis(1-tert-butoxycarbonyl)-aziridine；tert-butyl (2S)-2-[(1R,2R)-2-[(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]aziridin-2-yl]-1,2-bis(phenylmethoxy)ethyl]aziridine-1-carboxylate
• CAS: 156856-23-4
• 化学式: C₃₀H₄₀N₂O₆
• 分子量: 524.657
• InChiKey: OAOCQJPFEQZQJG-MADLMXHTSA-N

物化性质

• 沸点：
  599.2±30.0 °C(predicted)
• 密度：
  1.193±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  77.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis(1-tert-butoxycarbonyl)-aziridine 在 dilithium tetrabromonickelate(II) 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 12.5h， 生成 2,5-二(羟基甲基)-3,4-吡咯烷二醇
  参考文献：
  名称：

  Synthesis and evaluation as glycosidase inhibitors of 2,5-imino- d -glucitol and 1,5-imino- d -mannitol related derivatives

  摘要：

  Selectively functionalized 2,5-imino-D-glucitol and 1,5-imino-D-mannitol derivatives were synthesized and tested as precursors of hydrolytically resistant pseudo-disaccharides. Among them N-acetyl-6-amino-6-deoxy-2,5-imino-D-glucitol (11) and N-acetyl-6-amino-6-deoxy- 1,5-imino-D-mannitol (12) were found potent and specific inhibitors against beta-D-glucosidase and alpha-L-fucosidase, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00267-9
• 作为产物：
  描述：

  1,6-diazido-1,6-dideoxy-3,4-di-O-benzyl-D-mannitol 在 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 13.0h， 生成 (2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis(1-tert-butoxycarbonyl)-aziridine
  参考文献：
  名称：

  D-甘露糖醇衍生的双氮丙啶的2,5-二取代吡咯烷

  摘要：

  从D-甘露醇衍生的柔性L-Ido双氮丙啶开始，已经实现了3，4-二羟基-2，5-二取代的吡咯烷的精确合成。研究了苯硫醇盐和叠氮化物离子对N-Boc和N-Cbz活化的双氮丙啶核的亲核开环；该反应可以针对双开（衍生物A）或杂环化。杂环化导致对映纯的多取代的哌啶B和吡咯烷C的1：9混合物。

  DOI：

  10.1016/0040-4039(94)88023-9

文献信息

• Practical route to D-manno and D-gluco azasugars from C2 symmetric bis-aziridines
  作者：Isabelle McCort、Annie Duréault、Jean-Claude Depezay

  DOI：10.1016/0040-4039(96)01732-7

  日期：1996.10

  hydroxyl group, have been synthesized from the conformationally flexible N-Boc bis-aziridine 1. Regioselective ring-opening of 1 by acetic acid is a straight way towards 2, while reaction of 1 with water or allylic alcohol under ytterbium triflate catalysis produces selectively the azapyranose 3. Nitrous deamination carried out on the cyclic carbamate-protected pyrrolidine 4 leads to a 1:1 mixture of both

  由构型柔性的N -Boc双氮丙啶合成了被游离羟基取代的6-氨基-2,5-亚氨基-D-葡萄糖醇2和6-氨基-1,5-亚氨基-D-甘露糖醇3 1。乙酸对1的区域选择性开环是朝向2的直接方法，而在三氟甲磺酸催化下1与水或烯丙醇的反应则选择性地产生了氮杂吡喃糖3。在环状氨基甲酸酯保护的吡咯烷4上进行的亚硝酸脱氨基反应生成2,5-亚氨基-D-葡萄糖醇5和6的1：1混合物 在C-1或C-6带有一个游离羟基取代基。
• Concise synthesis of new homoazasugars. Fully substituted, functionally diverse pyrrolidines
  作者：Laurence Campanini、Annie Duréault、Jean-Claude Depezay

  DOI：10.1016/0040-4039(95)01674-7

  日期：1995.10

  Five-membered deoxyazasugars of D-gluco configuration, bearing an aminomethyl, a bromomelhyl or a thiomethyl group at the pseudo anomeric position, were prepared by nucleophilic opening of C2 symmetric bis-aziridines followed by chemoselective transformations of the nucleophile. The 1 -bromo-2 5-imino-D-glucitol 4 could be converted into attractive bicyclic compounds.

  通过C 2对称双氮丙啶核苷的亲核打开，然后进行亲核试剂的化学选择性转化，可以制备D-葡萄糖构型的五元脱氧氮杂三聚体，在假异头位置带有一个氨基甲基，一个溴甲基或一个硫代甲基。1 -bromo-2 5-亚氨基-D-葡萄糖醇4可以转化为有吸引力的双环化合物。
• New C2 symmetric bis-aziridines efficient synthesis of (2S,5S)-1,6-Di(p-toluenesulfonyloxy)-2,5-hexanediol, and (2S,3E,5S)-1,6-Di(p-toluenesulfonyloxy)-2,5-hexenediol
  作者：Juliette Fitremann、Annie Duréault、Jean-Claude Depezay

  DOI：10.1016/0040-4020(95)00533-e

  日期：1995.8

  The regioselective tosylation and functionalization of (S,S)-1,2,5,6-hexanetetrol is reported. The reductive aminocyclization of conformationally flexible diazidodiols by PPh(3) leads to C-2 symmetric bis-aziridines and to substituted furans.
• Yokomatsu, Tsutomu; Suemune, Kenji; Shibuya, Shiroshi, Heterocycles, 1993, vol. 35, # 2, p. 577 - 580
  作者：Yokomatsu, Tsutomu、Suemune, Kenji、Shibuya, Shiroshi

  DOI：——

  日期：——
• One step synthesis of sulfur and nitrogen linked aza-disaccharide precursors from D-mannitol derived bis-aziridines
  作者：Laurence Campanini、Annie Duréault、Jean-Claude Depezay

  DOI：10.1016/0040-4039(96)01033-7

  日期：1996.7

  Carbon-nitrogen and carbon-sulfur linked pseudodisaccharides incorporating an hydroxylated pyrrolidine type glucosidase inhibitor have been prepared. These new azasugar-containing disaccharides result from the nucleophilic opening of D-mannitol derived bis-aziridines either by 3-deoxy-3-amino-D-glucose or by 3-deoxy-3-thio-D-glucose. Copyright (C) 1996 Published by Elsevier Science Ltd