N-benzyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-allitol | 117859-47-9

• 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: N-benzyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-allitol
• 英文别名: N-benzyl-1,4-dideoxy-5,6-O-isopropylidene-1,4-imino-D-allitol；1,4-(benzylimino)-1,4-dideoxy-2,3-O-isopropylidene-D-allitol；2,3-O-Isopropylidene-1,4-dideoxy-1,4-benzylimino-D-allitol；(S)-1-((3AR,4R,6AS)-5-Benzyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-C]pyrrol-4-YL)-ethane-1,2-diol；(1S)-1-[(3aR,4R,6aS)-5-benzyl-2,2-dimethyl-3a,4,6,6a-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]ethane-1,2-diol
• CAS: 117859-47-9
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: OAAIPVBJEDNNJH-BARDWOONSA-N

物化性质

• 沸点：
  448.9±45.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-allitol 在 10 wt% Pd(OH)2 on carbon sodium tetrahydroborate 、 sodium periodate 、 水 、 氢气 、 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 8.0h， 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 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 110.0h， 生成 N-benzyl-1,4-dideoxy-1,4-imino-2,3-O-isopropylidene-D-allitol
  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

• Synthesis of New Aza-C-disaccharides Linking 4-Deoxy-4-amino-β-L-erythro-furanose to C-2 ofD-Glucose andD-Allose
  作者：Eliazar Rodríguez García、Margaret A. Brimble、Pierre Vogel

  DOI：10.1002/ejoc.200600199

  日期：2006.9

  that were converted into the aza-C-disaccharides (+)-4 [methyl 2-deoxy-2-(1,2,5-trideoxy-2,5-imino-L-ribitol-1C-yl)-α-D-glucopyranoside] and (+)-5 (the α-D-allopyranoside analogue). Reduction of the aldol and deprotection provided aza-C-disaccharide (+)-3 methyl 2-deoxy-2-[(1R or 1S)-2,5-dideoxy-2,5-imino-L-ribitol-1C-yl]-α-D-allopyranoside} with a hydroxymethano linker. (© Wiley-VCH Verlag GmbH &

  N-benzyl-2,5-dideoxy-2,5-imino-3,4-O-isopropylidene-L-ribose 与 4,6-O-benzylidene-2-deoxy-α-D-的交叉羟醛缩合erythro-hexopyranosid-3-ulose（烯醇钾 + HMPA）得到作为主要产物的醛醇。DAST 诱导的水消除产生两个烯酮，它们被转化为氮杂-C-二糖 (+)-4 [甲基 2-脱氧-2-(1,2,5-trideoxy-2,5-imino-L-ribitol- 1C-基)-α-D-吡喃葡萄糖苷]和(+)-5（α-D-别吡喃糖苷类似物）。醛醇的还原和脱保护提供氮杂-C-二糖 (+)-3 methyl 2-deoxy-2-[(1R or 1S)-2,5-dideoxy-2,5-imino-L-ribitol-1C- yl]-α-D-别吡喃糖苷}与羟基甲烷连接基。(© Wiley-VCH
• 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.
• 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.
• FLEET, GEORGE W. J.;SON, JONG CHAN, TETRAHEDRON, 44,(1988) N 9, C. 2637-2647
  作者：FLEET, GEORGE W. J.、SON, JONG CHAN

  DOI：——

  日期：——
• Heterocyclic compounds for inhibiting virus
  申请人：Monsanto Company

  公开号：EP0322395B1

  公开（公告）日：1993-03-24