(3aR,4R,6aS)-tert-butyl 4-((S)-1,2-dihydroxyethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate | 117956-54-4

• 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: (3aR,4R,6aS)-tert-butyl 4-((S)-1,2-dihydroxyethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate
• 英文别名: N-tert-butyloxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-allitol；N-tert-butoxycarbonyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-allitol；N-tert-butoxycarbonyl-1,4-dideoxy-5,6-O-isopropylidene-1,4-imino-D-allitol；N-tert-butiloxycarbonyl-1,4-dideoxy-5,6-O-isopropylidene-1,4-imino-D-allitol；tert-butyl (3aR,4R,6aS)-4-[(1S)-1,2-dihydroxyethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
• CAS: 117956-54-4
• 化学式: C₁₄H₂₅NO₆
• 分子量: 303.356
• InChiKey: XYSIRGYTUNWJCJ-YTWAJWBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aR,4R,6aS)-tert-butyl 4-((S)-1,2-dihydroxyethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate 在 sodium tetrahydroborate 、 sodium periodate 、 水 、 sodium hydride 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.0h， 生成 (2R,3R,4S)-2-([(9Z)-octadec-9-en-1-yloxy]methyl)pyrrolidine-3,4-diol
  参考文献：
  名称：

  [EN] NOVEL DIHYDROXYPYRROLIDINE DERIVATIVES AS ANTI-CANCER AGENTS
  [FR] NOUVEAUX DÉRIVÉS DE DIHYDROXYPYRROLIDINE EN TANT QU'AGENTS ANTICANCÉREUX

  摘要：

  公开号：

  WO2009118712A3
• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-D-gulitol 在 4-二甲氨基吡啶 、 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 114.5h， 生成 (3aR,4R,6aS)-tert-butyl 4-((S)-1,2-dihydroxyethyl)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate
  参考文献：
  名称：

  Polyhydroxylated pyrrolidines from sugar lactomes: Synthesis of 1,4-dideoxy-1,4-imino-d-glucitol from d-galactonolactone and syntheses of 1,4-dideoxy-1,4-imino-d-allitol, 1,4-dideoxy-1,4-imino-d-ribitol, and (2s,3r,4s)-3,4-dihydroxyproline from d-gulonolactone

  摘要：

  DOI：

  10.1016/s0040-4020(01)81716-6

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。
• Synthesis of a New C(1→2)-Linked Iminodisaccharide Starting from Levoglucosenone
  作者：Isabel Navarro、Pierre Vogel

  DOI：10.1002/1522-2675(200201)85:1<152::aid-hlca152>3.0.co;2-l

  日期：2002.1

  l)-alpha-D-glucopyr anoside ((+)-6) was obtained from the product of Nozaki-Kishi coupling of 2,5-[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropl-idene-L-ri bose ((-)-9) and 4-0-benzyl-6-O-[(benzyloxy)methyl]-3-deoxy-2-O-[(trifluoromethyl)sulfony l]-alpha-D-erythro-hex-2-enopyranosicle ((+)-12). The alkenyl triflato (+)-12 was derived from levoglucosenone (1).

  甲基 2-deoxy-2-[(1S)-2.5-dideoxy-2.5-imino-L-ribitol-1-C-yl)-α-D-glucopyranoside ((+)-6) 从2,5-[(tert-butoxy)carbonyl]imino}-2,5-dideoxy-3,4-O-isopropl-idene-L-ribose ((-)-9) 和 4 的 Nozaki-Kishi 偶联-0-benzyl-6-O-[(benzyloxy)methyl]-3-deoxy-2-O-[(trifluoromethyl)sulfony l]-alpha-D-erythro-hex-2-enopyranosicle ((+)-12) . 烯基三氟乙磺酸 (+)-12 衍生自左旋葡糖烯酮 (1)。
• Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as α-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies
  作者：Claudia Bello、Michele Cea、Giovanna Dal Bello、Anna Garuti、Ilaria Rocco、Gabriella Cirmena、Eva Moran、Aimable Nahimana、Michel A. Duchosal、Floriana Fruscione、Paolo Pronzato、Francesco Grossi、Franco Patrone、Alberto Ballestrero、Marc Dupuis、Bernard Sordat、Alessio Nencioni、Pierre Vogel

  DOI：10.1016/j.bmc.2010.03.009

  日期：2010.5

  Novel alpha-mannosidase inhibitors of the type (2R,3R,4S)-2-([(1R)-2- hydroxy-1-arylethyl]amine}methyl) pyrrolidine-3,4-diol have been prepared and assayed for their anticancer activities. Compound 30 with the aryl group = 4-trifluoromethylbiphenyl inhibits the proliferation of primary cells and cell lines of different origins, irrespective of Bcl-2 expression levels, inducing a G2/Mcell cycle arrest and by modification of genes involved in cell cycle progression and survival. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.
• Stereospecific Cyclization Strategies for α,ε-Dihydroxy-β-amino Esters: Asymmetric Syntheses of Imino and Amino Sugars
  作者：Stephen G. Davies、Emma M. Foster、James A. Lee、Paul M. Roberts、James E. Thomson

  DOI：10.1021/jo5018298

  日期：2014.10.17

  A range of biologically significant imino and amino sugars [1,4-dideoxy-1,4-imino-D-allitol, 3,6-dideoxy-3,6-imino-L-allonic acid, (3R,4S)-3,4-dihydroxy-L-proline, 1,5-anhydro-4-deoxy-4-amino-D-glucitol, and 1,5-anhydro-4-deoxy-4-amino-L-iditol] has been prepared via stereospecific cyclization of alpha,epsilon-dihydroxy-beta-amino esters. These substrates are readily prepared via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide to enantiopure alpha,beta-unsaturated esters (beta-substituted with cis- and trans-dioxolane units) coupled with in situ enolate oxidation with camphorsulfonyloxaziridine (CSO). Activation of the epsilon-hydroxyl group allowed cyclization to either the corresponding pyrrolidine or the tetrahydropyran scaffold, with the course of the cyclization process being dictated by the relative configuration of the dioxolane unit. When the alpha,epsilon-dihydroxy-beta-amino ester bears a cis-dioxolane unit, cyclization occurs upon attack of the beta-amino substituent to give the corresponding pyrrolidine after in situ N-debenzylation. In contrast, when the alpha,epsilon-dihydroxy-beta-amino ester bears a trans-dioxolane unit, cyclization occurs upon attack of the alpha-hydroxyl substituent to give the corresponding tetrahydropyran.