Trifluoro-methanesulfonic acid (3aS,5R,6S,6aS)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester | 133074-84-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoro-methanesulfonic acid (3aS,5R,6S,6aS)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• 英文别名: [(3aS,5R,6S,6aS)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] trifluoromethanesulfonate
• CAS: 133074-84-7
• 化学式: C₂₅H₃₁F₃O₇SSi
• 分子量: 560.664
• InChiKey: GRDFFXAVCOTVTG-MLNNCEHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  88.7
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (3aS,5R,6S,6aS)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 在 四丁基氟化铵 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 生成 3-deoxy-1,2-O-isopropylidene-5-O-p-toluenesulfonyl-β-D-threo-pentofuranose
  参考文献：
  名称：

  Deoxygenation at the C3 position of d- and l-arabinofuranose: stereospecific access to enantiomeric cordycepose derivatives

  摘要：

  Efficient synthesis of 3-deoxy-1,2-O-isopropylidene-beta-D- and beta-L-threo-pentofuranose (1,2-O-isopropylidene-beta-D- and beta-L-cordycepose) was accomplished starting from D- and L-arabinofuranose derivatives, respectively, by the action of LiBH(Et)(3) on corresponding intermediate 3-O-lyxofuranosyl trifluoromethanesulfonates. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.07.017
• 作为产物：
  描述：

  (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 在 吡啶 、 chromium(VI) oxide 、 sodium tetrahydroborate 、 乙酸酐 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.34h， 生成 Trifluoro-methanesulfonic acid (3aS,5R,6S,6aS)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
  参考文献：
  名称：

  Deoxygenation at the C3 position of d- and l-arabinofuranose: stereospecific access to enantiomeric cordycepose derivatives

  摘要：

  Efficient synthesis of 3-deoxy-1,2-O-isopropylidene-beta-D- and beta-L-threo-pentofuranose (1,2-O-isopropylidene-beta-D- and beta-L-cordycepose) was accomplished starting from D- and L-arabinofuranose derivatives, respectively, by the action of LiBH(Et)(3) on corresponding intermediate 3-O-lyxofuranosyl trifluoromethanesulfonates. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.07.017

文献信息

• Attempted ring contraction of α-triflates of 3-azido- and 3-fluoro-γ-lactones to oxetanes
  作者：R.P. Elliott、G.W.J. Fleet、K. Vogt、F.X. Wilson、Y. Wang、D.R. Witty、R. Storer、P.L. Myers、C.J. Wallis

  DOI：10.1016/s0957-4166(00)82381-2

  日期：1990.1
• Deoxygenation at the C3 position of d- and l-arabinofuranose: stereospecific access to enantiomeric cordycepose derivatives
  作者：Fábio da Paixão Soares、Maria Joselice e Silva、Bogdan Doboszewski

  DOI：10.1016/j.carres.2013.07.017

  日期：2013.10

  Efficient synthesis of 3-deoxy-1,2-O-isopropylidene-beta-D- and beta-L-threo-pentofuranose (1,2-O-isopropylidene-beta-D- and beta-L-cordycepose) was accomplished starting from D- and L-arabinofuranose derivatives, respectively, by the action of LiBH(Et)(3) on corresponding intermediate 3-O-lyxofuranosyl trifluoromethanesulfonates. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.