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 | 222166-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 222166-95-2
• 化学式: C₃₉H₅₈N₆O₁₇
• 分子量: 882.92
• InChiKey: WXQZSQZNTIYNIZ-GXCOQCSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  62
• 可旋转键数：
  14
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  239
• 氢给体数：
  3
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  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 在 钯 氢气 作用下， 以 异丙醇 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Helix-Forming Carbohydrate Amino Acids

  摘要：

  [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.

  DOI：

  10.1021/jo0480040
• 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 、 sodium hydroxide 、 氢气 、 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

文献信息

• An octameric carbopeptoid; secondary structure in octameric and tetrameric 5-aminomethyl-tetrahydrofuran-2-carboxylates
  作者：Timothy D.W. Claridge、Daniel D. Long、Natasha L. Hungerford、Robin T. Aplin、Martin D. Smith、Daniel G. Marquess、George W.J. Fleet

  DOI：10.1016/s0040-4039(99)00111-2

  日期：1999.3

  The efficient synthesis of an octameric furanose carbopeptoid, readily purified by chromatography in ethyl acetate:hexane (2:1), is reported. Extensive NMR studies suggest that two tetrameric 5-aminomethyltetrahydrofuran-2-carboxylate are prone to adopt solution conformations reminiscent of a repeating beta-turn, a third tetramer and the corresponding octamer may tend towards a left-handed alpha-helix. (C) 1999 Elsevier Science Ltd. All rights reserved.