(2S,3R,4S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-trifluoromethanesulfonyloxy-tetrahydro-furan-2-carboxylic acid isopropyl ester | 1054611-42-5

• 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: (2S,3R,4S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-trifluoromethanesulfonyloxy-tetrahydro-furan-2-carboxylic acid isopropyl ester
• 英文别名: propan-2-yl (2S,3R,4S)-3-[tert-butyl(diphenyl)silyl]oxy-4-(trifluoromethylsulfonyloxy)oxolane-2-carboxylate
• CAS: 1054611-42-5
• 化学式: C₂₅H₃₁F₃O₇SSi
• 分子量: 560.664
• InChiKey: CDFXVFQIRKHMFH-FKBYEOEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 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：

  (2S,3R,4S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-trifluoromethanesulfonyloxy-tetrahydro-furan-2-carboxylic acid isopropyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以3.02 g的产率得到isopropyl 2,5-anhydro-4-azido-3-O-tert-butyldiphenylsilyl-4-deoxy-L-ribonate
  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
• 作为产物：
  描述：

  methyl 2,5-anhydro-D-arabinoate 在 吡啶 、 咪唑 、 盐酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 58.0h， 生成 (2S,3R,4S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-trifluoromethanesulfonyloxy-tetrahydro-furan-2-carboxylic acid isopropyl ester
  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

• 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.