isopropyl 2,5-anhydro-6-azido-6-deoxy-3,4-O-isopropylidene-D-talonate | 222317-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl 2,5-anhydro-6-azido-6-deoxy-3,4-O-isopropylidene-D-talonate
• 英文别名: propan-2-yl (3aS,4S,6R,6aS)-6-(azidomethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylate
• CAS: 222317-55-7
• 化学式: C₁₂H₁₉N₃O₅
• 分子量: 285.3
• InChiKey: MFPVQFDFTCZFPE-KATARQTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  isopropyl 2,5-anhydro-6-azido-6-deoxy-3,4-O-isopropylidene-D-talonate 在 钯 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 二氯甲烷 、 异丙醇 为溶剂， 反应 45.0h， 生成 (3aS,4S,6R,6aS)-6-{[((3aS,4S,6R,6aS)-6-Aminomethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbonyl)-amino]-methyl}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid isopropyl ester
  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 盐酸 作用下， 以 异丙醇 为溶剂， 反应 6.0h， 生成 isopropyl 2,5-anhydro-6-azido-6-deoxy-3,4-O-isopropylidene-D-talonate
  参考文献：
  名称：

  Open-chain acetonides of D-galactono-1,4-lactone as starting materials for pyrrolidines, azepanes and 5-azidomethyltetrahydrofuran-2-carboxylates: monomers for polyhydroxylated nylon and for tetrahydrofuran carbopeptoids

  摘要：

  在丙酮中，在二甲氧基丙烷和托西酸的作用下，D-半乳糖酸-1,4-内酯可分别生成20%和78%的甲基2,3:5,6-二-O-异亚丙基-D-半乳糖酸酯6（仅C-4上的次羟基未受保护）和甲基2,3:4,5-二-O-异亚丙基-D-半乳糖酸酯5（仅C-6上的主羟基未受保护）。1,4-二脱氧-1,4-亚氨基-D-葡萄糖醇16（一种吡咯烷）的合成以及6-叠氮-6-脱氧-D-半乳糖酸-1,4-内酯22的高效制备都说明了这种易得中间体的价值。将22转化为七元半乳糖内酰胺21（一种四羟基己内酰胺）可得到羟基化尼龙聚合物。半乳糖内酰胺21对多种糖苷酶没有明显的抑制作用。22与三氟甲磺酸酐反应可生成两种外消旋5-（叠氮甲基）四氢呋喃-2-羧酸酯，它们可作为两种系列碳青霉烯类药物的起始原料

  DOI：

  10.1039/a809807g

文献信息

• From sequencamers to foldamers? Tetrameric furanose carbopeptoids from cis- and trans-5-aminomethyl-tetrahydrofuran-2-carboxylates
  作者：Daniel D. Long、Natasha L. Hungerford、Martin D. Smith、Dominic E.A. Brittain、Daniel G. Marquess、Timothy D.W. Claridge、George W.J. Fleet

  DOI：10.1016/s0040-4039(99)00110-0

  日期：1999.3

  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.