2,5-ANHYDRO-3,4,6-TRI-O-BENZYL-尾-D-ALLONONITRILE | 82267-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,5-ANHYDRO-3,4,6-TRI-O-BENZYL-尾-D-ALLONONITRILE
• 英文名称: 2,3,5-tri-O-benzyl-β-D-ribofuranosyl cyanide
• 英文别名: (2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane-2-carbonitrile
• CAS: 82267-01-4
• 化学式: C₂₇H₂₇NO₄
• 分子量: 429.516
• InChiKey: PQATZWNKXOJHJA-YYGZZXRFSA-N

物化性质

• 沸点：
  594.1±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-ANHYDRO-3,4,6-TRI-O-BENZYL-尾-D-ALLONONITRILE 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 10 wt% Pd(OH)2 on carbon 、 三乙胺盐酸盐 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 环己烯 为溶剂， 反应 39.0h， 生成
  参考文献：
  名称：

  Synthesis of novel tetrazole C5-linked C0- and C2-ribonucleoside phosphoramidites using MePOM and POM groups for probing RNA catalysis

  摘要：

  Novel C5-linked C-0- and C-2-tetrazole ribonucleoside phosphoramidites were designed and synthesized via tetrazole C-nucleosides. Pivaloyloxymethyl (POM) and methyl-substituted POM (MePOM) groups were introduced as N-protecting groups in the tetrazole ring that can be readily removed under mild basic conditions. The phosphoramidites were successfully incorporated into the VS ribozyme substrate and hence providing a chemogenetic approach to determine which nucleobases of ribozymes function as the acid or base, in the studies of ribozyme general acid and base catalysis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.082
• 作为产物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃核糖 在 4-二甲氨基吡啶 、 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 2,5-ANHYDRO-3,4,6-TRI-O-BENZYL-尾-D-ALLONONITRILE
  参考文献：
  名称：

  WO2020157694A5

  摘要：

  公开号：

  WO2020157694A5

文献信息

• TMSN3-Bu2Sn(OAc)2: A modified and mild reagent system for Wittenberger tetrazole-synthesis
  作者：Hiroki Yoneyama、Naoki Oka、Yoshihide Usami、Shinya Harusawa

  DOI：10.1016/j.tetlet.2019.151517

  日期：2020.2

  Treatments of various nitriles with TMSN3 and Bu2Sn(OAc)2 at 30 oC in benzene for 60 h yielded the corresponding 5-substituted 1H-tetrazoles in good to excellent yields. This method is a mild and efficient alternative reagent system for Wittenberger tetrazole-synthesis that uses TMSN3 and Bu2SnO in toluene at high temperature (93–110 °C) for 24–72 h.

  各种腈与TMSN的处理3和卜2的Sn（OAc）2在30 ö下在苯60小时，得到相应的5-取代的1 ħ在良好-tetrazoles到优异的产率。该方法是温和有效的Wittenberger四唑合成的替代试剂系统，该系统在高温（93–110°C）下使用甲苯中的TMSN 3和Bu 2 SnO持续24–72 h。
• [EN] COMPOUNDS, PHARMACEUTICAL COMPOSITIONS AND USE THEREOF AS INHIBITORS OF RAN GTPASE<br/>[FR] COMPOSÉS, COMPOSITIONS PHARMACEUTIQUES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE LA RAN GTPASE
  申请人：THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIV

  公开号：WO2019046931A1

  公开（公告）日：2019-03-14

  Compounds of general formula IA, IB and IC outlined below, including pharmaceutically acceptable salts, solvates and hydrates thereof. Such compounds and pharmaceutical compositions comprising them may be used in medical conditions involving Ran GTPase.

  以下概述了通式IA、IB和IC的化合物，包括其药用盐、溶剂合物和水合物。这些化合物和包含它们的药物组合物可用于涉及Ran GTP酶的医疗状况。
• Highly stereoselective synthesis of aryl/heteroaryl-<i>C</i>-nucleosides <i>via</i> the merger of photoredox and nickel catalysis
  作者：Yingying Ma、Shihui Liu、Yifan Xi、Hongrui Li、Kai Yang、Zhihao Cheng、Wei Wang、Yongqiang Zhang

  DOI：10.1039/c9cc07184a

  日期：——

  developed. The reaction proceeds smoothly under visible-light irradiation and features the using of cost-effective and easily handled catalysts and starting materials, which allows the highly stereoselective synthesis of diverse aryl/heteroaryl-C-nucleosides in moderate to high yields.

  已经开发了异核糖基/脱氧核糖基酸与芳基/杂芳基溴化物的光氧化还原/镍双催化的脱羧交叉偶联反应。该反应在可见光照射下可顺利进行，其特点是使用经济高效且易于操作的催化剂和起始原料，从而可以以中等至高收率高度立体选择性地合成各种芳基/杂芳基-C-核苷。
• A convenient synthesis of C-α-d-ribofuranosyl compounds from 1-O-acetyl-2,3,5-tri-O-benzyl-β-d-ribose by the promotion of triphenylmethyl perchlorate
  作者：Teruaki Mukaiyama、Shū Kobayashi

  DOI：10.1016/s0008-6215(00)90880-2

  日期：1987.12

  trimethylsilyl cyanide, to give the corresponding C-α- d -ribofuranosyl derivatives in excellent yields. Similarly, a C-α- d -ribofuranosyl compound was obtained stereoselectively in high yield by use of a flow system with polymer-supported triphenylmethyl perchlorate, prepared from polystyrene-bound triphenylmethanol, packed in a glass-tube column.

  摘要在催化量的高氯酸三苯甲基酯（高氯酸三苯甲基酯）存在下，1-O-乙酰基-2,3,5-三-O-苄基-β-d-核糖与三甲基甲硅烷基亲核试剂如三甲基甲硅烷基烯醇醚立体选择性地反应烯丙基硅烷和三甲基甲硅烷基氰化物，以优异的收率得到相应的C-α-d-核呋喃呋喃糖基衍生物。类似地，通过使用由载有聚苯乙烯结合的三苯基甲醇的聚合物支撑的高氯酸三苯甲基酯的流动系统，通过填充在玻璃管柱中的流动系统，以高收率立体选择性地获得C-α-d-呋喃核糖基化合物。
• A FACILE SYNTHESIS OF α-C-RIBOFURANOSIDES FROM 1-O-ACETYL RIBOSE IN THE PRESENCE OF TRITYL PERCHLOLATE
  作者：Teruaki Mukaiyama、Shu Kobayashi、Shin-ichiro Shoda

  DOI：10.1246/cl.1984.1529

  日期：1984.9.5

  In the presence of a catalytic amount of trityl perchlorate, 1-O-acetyl ribose stereoselectively reacts with silylated nucleophiles, such as silyl enol ether, allylsilane, and trimethylsilyl cyanide, to give the corresponding α-C-ribofuranosides in excellent yields.

  在催化量的三苯甲基过氯酸盐存在下，1-O-乙酰核糖与硅化亲核试剂（如硅基烯醇醚、烯丙基硅烷和三甲基硅基氰化物）发生立体选择性反应，生成相应的α-C-核糖呋喃苷，并且产率极高。