methyl 2,5-anhydro-4-azido-4-deoxy-L-xylonate | 605668-43-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 2,5-anhydro-4-azido-4-deoxy-L-xylonate
• 英文别名: methyl (2S,3R,4S)-4-azido-3-hydroxyoxolane-2-carboxylate
• CAS: 605668-43-7
• 化学式: C₆H₉N₃O₄
• 分子量: 187.155
• InChiKey: TXYMFIPRNQSXPJ-LMVFSUKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,5-anhydro-4-azido-4-deoxy-L-xylonate 在 palladium on activated charcoal 氢氧化钾 、 水 、 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 57.0h， 生成 isopropyl 2,5-anhydro-4-N-(2,5-anhydro-4-N-(2,5-anhydro-4-N-(2,5-anhydro-4-azido-4-deoxy-L-xylonamido)-4-deoxy-L-xylonamido)-4-deoxy-L-xylonamido)-4-deoxy-L-xylonate
  参考文献：
  名称：

  A novel series of oligomers from 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans stereochemistry

  摘要：

  Two tetrahydrofuran-based y-amino acids [2,4-cis and 2,4-trans] were subjected to iterative peptide-coupling procedures to afford dimeric, tetrameric and hexameric carbopeptoids in good yield. These homooligomers were prepared for secondary structural study-to ascertain the conformational preference inherent in the monomer units. The L-xylo oligomers were protected with triethylsilyl ethers to increase the range of solvents suitable for structural investigation. Initial secondary structure data indicate the presence of hydrogen-bonded conformations in the L-ribo series. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.067
• 作为产物：
  描述：

  3,4-O-benzylidene-2-O-trifluoromethanesulfonyl-D-ribono-1,5-lactone 在 吡啶 、 盐酸 、 sodium azide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 95.0h， 生成 methyl 2,5-anhydro-4-azido-4-deoxy-L-xylonate
  参考文献：
  名称：

  Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships

  摘要：

  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.

  DOI：

  10.1016/j.tet.2006.02.007

文献信息

• 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.
• 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.
• A novel series of oligomers from 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans stereochemistry
  作者：Alison A. Edwards、Gangadharar J. Sanjayan、Shuji Hachisu、George E. Tranter、George W.J. Fleet

  DOI：10.1016/j.tet.2006.05.067

  日期：2006.8

  Two tetrahydrofuran-based y-amino acids [2,4-cis and 2,4-trans] were subjected to iterative peptide-coupling procedures to afford dimeric, tetrameric and hexameric carbopeptoids in good yield. These homooligomers were prepared for secondary structural study-to ascertain the conformational preference inherent in the monomer units. The L-xylo oligomers were protected with triethylsilyl ethers to increase the range of solvents suitable for structural investigation. Initial secondary structure data indicate the presence of hydrogen-bonded conformations in the L-ribo series. (c) 2006 Elsevier Ltd. All rights reserved.