isopropyl 6-amino-2,5-anhydro-6-deoxy-3,4-O-isopropylidene-D-talonate | 222317-65-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 6-amino-2,5-anhydro-6-deoxy-3,4-O-isopropylidene-D-talonate
• 英文别名: propan-2-yl (3aS,4S,6R,6aS)-6-(aminomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
• CAS: 222317-65-9
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: ONUKQENHBPBKLJ-KATARQTJSA-N

物化性质

• 沸点：
  327.027±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.126±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  isopropyl 6-amino-2,5-anhydro-6-deoxy-3,4-O-isopropylidene-D-talonate 在 sodium hydroxide 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 propan-2-yl (3aS,4S,6R,6aS)-6-[[[(3aS,4S,6R,6aS)-6-[[[(3aS,4S,6R,6aS)-6-[[[(3aS,4S,6R,6aS)-6-(azidomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carbonyl]amino]methyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carbonyl]amino]methyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carbonyl]amino]methyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
  参考文献：
  名称：

  From sequencamers to foldamers? Tetrameric furanose carbopeptoids from cis- and trans-5-aminomethyl-tetrahydrofuran-2-carboxylates

  摘要：

  The synthesis of three stereoisomeric cis- and trans-5-azidomelhyl-tetrahydrofuran-2-carboxylates in which a ketal-protected cis-diol unit is present is described. The monomers undergo efficient oligomerisation to tetrameric carbopeptoids in which the diol protection facilitates ready purification by chromatography which augurs well for the formation of homogeneous higher polymers. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00110-0
• 作为产物：
  描述：

  (2S,3S,4R)-5-Azidomethyl-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methyl ester 在 钯 盐酸 、 氢气 作用下， 生成 isopropyl 6-amino-2,5-anhydro-6-deoxy-3,4-O-isopropylidene-D-talonate
  参考文献：
  名称：

  From sequencamers to foldamers? Tetrameric furanose carbopeptoids from cis- and trans-5-aminomethyl-tetrahydrofuran-2-carboxylates

  摘要：

  The synthesis of three stereoisomeric cis- and trans-5-azidomelhyl-tetrahydrofuran-2-carboxylates in which a ketal-protected cis-diol unit is present is described. The monomers undergo efficient oligomerisation to tetrameric carbopeptoids in which the diol protection facilitates ready purification by chromatography which augurs well for the formation of homogeneous higher polymers. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00110-0

文献信息

• Helix-Forming Carbohydrate Amino Acids
  作者：Timothy D. W. Claridge、Daniel D. Long、Christopher M. Baker、Barbara Odell、Guy H. Grant、Alison A. Edwards、George E. Tranter、George W. J. Fleet、Martin D. Smith

  DOI：10.1021/jo0480040

  日期：2005.3.1

  [GRAPHICS]The solution-phase conformational properties of tetrameric and octameric chains of C-glycosyl alpha-D-lyxofuranose configured tetrahydrofuran amino acids (where the C-2 and C-5 substituents on the tetrahydrofuran ring are trans to each other) were examined using NMR and IR and CD in organic solvents. Studies by NMR and IR demonstrated that in chloroform solution, the tetramer 7 does not adopt a hydrogen-bonded conformation whereas the octamer 10 populates a well-defined helical secondary structure stabilized by 16-membered (i, i - 3) interresidue hydrogen bonds, similar to a pi-helix. Circular dichroism studies in trifluoroethanol are consistent with this conformation for the octamer 10, and also indicate that the tetramer 7 adopts a rigid conformation not stabilized by hydrogen bonds.