methyl 2,5-anhydro-3,4-O-isopropylidene-L-ribonate | 605668-29-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,5-anhydro-3,4-O-isopropylidene-L-ribonate
• 英文别名: methyl (3aS,4S,6aS)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
• CAS: 605668-29-9
• 化学式: C₉H₁₄O₅
• 分子量: 202.207
• InChiKey: BNXZYVHESXVNKO-ACZMJKKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,5-anhydro-3,4-O-isopropylidene-L-ribonate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以89%的产率得到methyl 2,5-anhydro-3,4-O-isopropylidene-L-arabinoate
  参考文献：
  名称：

  Templated scaffolds of cis- and trans-tetrahydrofuran γ-amino acids: γ-azido-β-hydroxy-tetrahydrofuran-2-carboxylates from pentono-δ-lactones

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(03)01415-1
• 作为产物：
  描述：

  3,4-O-isopropylidine L-arabinopyranose 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 15.5h， 生成 methyl 2,5-anhydro-3,4-O-isopropylidene-L-ribonate
  参考文献：
  名称：

  Templated scaffolds of cis- and trans-tetrahydrofuran γ-amino acids: γ-azido-β-hydroxy-tetrahydrofuran-2-carboxylates from pentono-δ-lactones

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(03)01415-1

文献信息

• 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.