3,4-O-benzylidene-2-O-trifluoromethanesulfonyl-D-ribono-1,5-lactone | 104945-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4-O-benzylidene-2-O-trifluoromethanesulfonyl-D-ribono-1,5-lactone
• 英文别名: Trifluoro-methanesulfonic acid 6-oxo-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester；[(2R,3aR,7R,7aR)-6-oxo-2-phenyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl] trifluoromethanesulfonate
• CAS: 104945-87-1
• 化学式: C₁₃H₁₁F₃O₇S
• 分子量: 368.287
• InChiKey: CQTSKCCAINXKOS-DNRKLUKYSA-N

物化性质

• 熔点：
  140.9-142.5 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  494.5±45.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3,4-O-benzylidene-2-O-trifluoromethanesulfonyl-D-ribono-1,5-lactone 在 叠氮化锂 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以77%的产率得到2-azido-3,4-O-benzylidene-2-deoxy-D-arabinono-1,5-lactone
  参考文献：
  名称：

  β-羟基叠氮化物的自由基断裂合成高度官能化的手性腈。将醛腈方便地转化为1,4-和1,5-氨基醛糖醇

  摘要：

  描述了通过环β-羟基叠氮化物的烷氧基自由基断裂来合成高度官能化的腈。烷氧基是通过醇与（二乙酰氧基碘）苯和碘在与敏感取代基和碳水化合物化学中最常使用的保护基团相容的温和条件下反应生成的。为了探究这种方法的范围和限制，进行实验使用各种碳水化合物的β羟基的叠氮化物的（1 - 6，33，和41），单萜（21和22），和类固醇（23 - 25）天然产品系列。特别令人感兴趣的是aldopentonitriles（15 - 18，34，和42）和aldotetrononitriles（19和20从相应的2-叠氮基-2- deoxycarbohydrates合成）。为了证明这些醛腈作为手性合成子的多功能性，制备了多羟基吡咯烷和-哌啶型的1，4-亚氨基-1-脱氧糖（37）和1，5-亚氨基-1-脱氧糖（43）类似物。

  DOI：

  10.1021/jo049026p
• 作为产物：
  描述：

  D-(+)-核糖酸-1,4-内酯 在 盐酸 作用下， 以 吡啶 为溶剂， 生成 3,4-O-benzylidene-2-O-trifluoromethanesulfonyl-D-ribono-1,5-lactone
  参考文献：
  名称：

  Synthesis of 2R,3S,4R-dihydroxyproline from D-ribonolactone

  摘要：

  DOI：

  10.1016/s0040-4039(00)84754-1

文献信息

• Baird, Peter D.; Dho, Jonathan C.; Fleet, George W. J., Journal of the Chemical Society. Perkin transactions I, 1987, p. 1785 - 1792
  作者：Baird, Peter D.、Dho, Jonathan C.、Fleet, George W. J.、Peach, Josephine M.、Prout, Keith、Smith, Paul W.

  DOI：——

  日期：——
• Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships
  作者：Alison A. Edwards、Gangadharar J. Sanjayan、Shuji Hachisu、Raquel Soengas、Alistair Stewart、George E. Tranter、George W.J. Fleet

  DOI：10.1016/j.tet.2006.02.007

  日期：2006.4

  Templated tetrahydrofuran-based gamma-azido esters were prepared with the C-2 and C-4 functionalities in cis and trans relative configurations. This was achieved by ring contraction of the suitably protected 2-O-triflates of pentono-1,5-lactones (D-ribose and L-arabinose) with subsequent introduction of the azide via the 4-O-triflate. Access to a corresponding beta-azido ester was achieved in good yield. Little elimination product was observed by introduction of the azide via the 3-O-triflate. These azido esters are scaffolds. which may be predisposed to adopt secondary structural motifs, for example. for use as peptidomimetics; they may also be utilised for the preparation of stereodiverse compound libraries. (c) 2006 Elsevier Ltd All rights reserved.
• Templated scaffolds of cis- and trans-tetrahydrofuran γ-amino acids: γ-azido-β-hydroxy-tetrahydrofuran-2-carboxylates from pentono-δ-lactones
  作者：Gangadharar J. Sanjayan、Alistair Stewart、Shuji Hachisu、Raquel Gonzalez、Mark P. Watterson、George W.J. Fleet

  DOI：10.1016/s0040-4039(03)01415-1

  日期：2003.7

  Short syntheses of enantiomeric templated scaffolds of cis- and trans-tetrahydrofuran gamma-amino acids from pentono-delta-lactones derived from arabinose and ribose are reported; an unexpectedly efficient synthesis of a templated tetrahydrofuran beta-amino acid by azide displacement of a triflate beta to an ester function proceeds with remarkably little elimination. These materials should allow evaluation of such peptidomimetics to induce predisposition towards secondary structures. (C) 2003 Elsevier Ltd. All rights reserved.
• High yield reduction of 2-O-trifluoromethanesulphonate esters of α-hydroxylactones to the corresponding 2-deoxylactones by lithium iodide trihydrate
  作者：Russell P. Elliott、George W.J. Fleet、Soo Gyoung Young、Nigel G. Ramsden、Colin Smith

  DOI：10.1016/s0040-4039(00)97471-9

  日期：——
• BAIRD, PETER D.;DHO, JONATHAN C.;FLEET, GEORGE W. J.;PEACH, JOSEPHINE M.;+, J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 8, 1785-1791
  作者：BAIRD, PETER D.、DHO, JONATHAN C.、FLEET, GEORGE W. J.、PEACH, JOSEPHINE M.、+

  DOI：——

  日期：——