1-(5-O-triphenylmethyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-5-bromoindoline | 791609-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-(5-O-triphenylmethyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-5-bromoindoline
• 英文别名: 1-[(3aR,4S,6R,6aR)-2,2-dimethyl-6-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-bromo-2,3-dihydroindole
• CAS: 791609-48-8
• 化学式: C₃₅H₃₄BrNO₄
• 分子量: 612.563
• InChiKey: VKZHXYNMIYMFMO-IGUZCVLDSA-N

物化性质

• 沸点：
  685.5±55.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(5-O-triphenylmethyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-5-bromoindoline 在 manganese(IV) oxide 、 4 A molecular sieve 作用下， 以 苯 为溶剂， 反应 3.0h， 以90%的产率得到5-Bromo-1-((3aR,4S,6R,6aR)-2,2-dimethyl-6-trityloxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-1H-indole
  参考文献：
  名称：

  α-二氢吲哚核苷的低温脱氢

  摘要：

  使用二氧化锰和分子筛在苯或二氯甲烷中，由α-二氢吲哚核苷可轻松以优异的收率和适中的温度从α-二氢吲哚核苷制备各种α-吲哚核苷。

  DOI：

  10.1016/j.tetlet.2004.08.110
• 作为产物：
  描述：

  5-溴二氢吲哚 在 正丁基锂 、 2-氟-1-甲基吡啶翁对甲苯磺酸盐 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 1-(5-O-triphenylmethyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-5-bromoindoline
  参考文献：
  名称：

  Regioselective Glycosylation: Synthesis of α-Indoline Nucleosides

  摘要：

  Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivily in 90-96% yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY COSY and HMQC) NMR spectroscopy.

  DOI：

  10.1081/ncn-200067398

文献信息

• Low temperature dehydrogenation of α-indoline nucleosides
  作者：Tilak Chandra、Shawn Zou、Kenneth L. Brown

  DOI：10.1016/j.tetlet.2004.08.110

  日期：2004.10

  A variety of α-indole nucleosides are easily prepared from α-indoline nucleosides in excellent yield and at moderate temperature using manganese dioxide and molecular sieves in benzene or methylene chloride.

  使用二氧化锰和分子筛在苯或二氯甲烷中，由α-二氢吲哚核苷可轻松以优异的收率和适中的温度从α-二氢吲哚核苷制备各种α-吲哚核苷。
• Direct glycosylation: synthesis of α-indoline ribonucleosides
  作者：Tilak Chandra、Kenneth L. Brown

  DOI：10.1016/j.tetlet.2005.01.164

  日期：2005.3

  A selective synthesis of alpha-anomers of indoline nucleosides is described. Ribonucleosides of indoline, dimethylindoline and 5-bromoindoline are readily prepared in good yield by reacting indoline bases directly with the protected sugar, 2,3-O-(1-methylethylidene) 5-O-(triphenylmethyl)-D-ribofuranose in dry ethanol or methylene chloride in presence of molecular sieves at 40-60 degrees C. (C) 2005 Elsevier Ltd. All rights reserved.
• Regioselective Glycosylation: Synthesis of <i>α</i>-Indoline Nucleosides
  作者：Kenneth L. Brown、Tilak Chandra、Shawn Zou、Edward J. Valente

  DOI：10.1081/ncn-200067398

  日期：2005.7.1

  Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivily in 90-96% yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY COSY and HMQC) NMR spectroscopy.