(S)-3-(1H-Indol-3-yl)-2-[((2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-tetrahydro-pyran-2-ylmethyl)-amino]-propionic acid methyl ester | 135754-32-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-(1H-Indol-3-yl)-2-[((2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-tetrahydro-pyran-2-ylmethyl)-amino]-propionic acid methyl ester
• CAS: 135754-32-4
• 化学式: C₁₈H₂₄N₂O₇
• 分子量: 380.398
• InChiKey: MJLZQDCQGZREEJ-VNIVASGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.36
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  144.27
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  (S)-3-(1H-Indol-3-yl)-2-[((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl)-amino]-propionic acid methyl ester 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 2.0h， 以69.6%的产率得到(S)-3-(1H-Indol-3-yl)-2-[((2R,3S,4R,5R)-2,3,4,5-tetrahydroxy-tetrahydro-pyran-2-ylmethyl)-amino]-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of aromatic Amadori compounds

  摘要：

  A series of O-isopropylidene protected aromatic Amadori compounds [N-(1-deoxy-D-fructos-1-yl)-L-amino acid esters] were synthesized by reacting 2,3:4,5-di-O-isopropylidene-1-O-(trifluoromethanesulfonyl)-D-fructopyranose with alkyl esters of L-phenylalanine, L-tyrosine, and L-tryptophan. The Amadori compounds were obtained in much higher yields than those previously reported due to utilizing triflate as an extremely reactive leaving group at C-1 of the sugar reagent. The triflate derivative was prepared in high yield using the sterically hindered, non-nucleophilic base, 2,6-di-tert-butyl-4-methylpyridine, as proton acceptor. The Amadori compounds were characterized by H-1- or C-13-n.m.r. spectroscopy, as well as by i.r. and mass spectroscopy. C-13-n.m.r. spectroscopy was used to study the equilibria among the various ring forms of the free-hydroxy D-fructose tryptophan compound.

  DOI：

  10.1016/0008-6215(91)84043-e