(2S,3S,4R)-5-Azidomethyl-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methyl ester | 222317-60-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R)-5-Azidomethyl-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methyl ester
• CAS: 222317-60-4
• 化学式: C₇H₁₁N₃O₅
• 分子量: 217.181
• InChiKey: RUVRDQHMXBWCLJ-KUZWUUJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.04
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  124.75
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  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 (3aS,4S,6R,6aS)-6-{[((3aS,4S,6R,6aS)-6-Azidomethyl-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
  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：

  甲醇 、 6-azido-6-deoxy-D-galactono-1,4-lactone 在 吡啶 、 三氟甲磺酸酐 作用下， 生成 (2S,3S,4R)-5-Azidomethyl-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid methyl ester
  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

• 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
  作者：Daniel D. Long、Rebecca J. E. Stetz、Robert J. Nash、Daniel G. Marquess、Janet D. Lloyd、Ana L. Winters、Naoki Asano、George W. J. Fleet

  DOI：10.1039/a809807g

  日期：——

  Treatment of D-galactono-1,4-lactone with dimethoxypropane in acetone in the presence of tosic acid forms methyl 2,3:5,6-di-O-isopropylidene-D-galactonate 6 (with only the secondary hydroxy group at C-4 unprotected) and methyl 2,3:4,5-di-O-isopropylidene-D-galactonate 5 (with only the primary hydroxy group at C-6 unprotected) in yields of 20% and 78%, respectively. The value of such easily accessible intermediates is illustrated by the synthesis of 1,4-dideoxy-1,4-imino-D-glucitol 16 (a pyrrolidine), and for the efficient preparation of 6-azido-6-deoxy-D-galactono-1,4-lactone 22. The conversion of 22 to a seven-membered galactonolactam 21 (a tetrahydroxycaprolactam) may provide access to hydroxylated nylon polymers. The galactonolactam 21 has no significant inhibitory effect on a number of glycosidases. Reaction of 22 with triflic anhydride gives two epimeric 5-(azidomethyl)tetrahydrofuran-2-carboxylates which provide starting materials for two series of carbopeptoids, one of which probably has a helical structure and the other a structure reminiscent of a β-turn.

  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