(S)-2-Amino-3-{1-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-yl]-1H-indol-3-yl}-propionic acid | 666855-49-8

• 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)-2-Amino-3-{1-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-yl]-1H-indol-3-yl}-propionic acid
• CAS: 666855-49-8
• 化学式: C₂₈H₃₆N₂O₁₁
• 分子量: 576.601
• InChiKey: QDVXIQWJSKSMLS-MOJIEUQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  41.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  182.68
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Amino-3-{1-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-yl]-1H-indol-3-yl}-propionic acid 在 甲胺 作用下， 以77%的产率得到N¹-(β-D-glucopyranosyl-⁴C₁)-L-tryptophan
  参考文献：
  名称：

  Synthesis of tryptophan N -glucoside

  摘要：

  The naturally occurring L-tryptophan N-glucoside was synthesized using 2-O-pivaloylated glucosyl trichloroacetimidate, which gave beta-N-In-glucosides. From 2-O-acetylated donors only tryptophan-1-yl-ethylidene compounds (amide acetals) were obtained. The employment of alpha-azido L-tryptophan benzyl ester facilitated purification and deprotection and improved the yields of the glycosylation step. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.190
• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-2-[3-[(2S)-2-azido-3-oxo-3-phenylmethoxypropyl]indol-1-yl]oxan-3-yl] 2,2-dimethylpropanoate 在 palladium(II) oxide 、 氢气 作用下， 以 甲醇 为溶剂， 以42%的产率得到(S)-2-Amino-3-{1-[(2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2-dimethyl-propionyloxy)-tetrahydro-pyran-2-yl]-1H-indol-3-yl}-propionic acid
  参考文献：
  名称：

  Synthesis of tryptophan N -glucoside

  摘要：

  The naturally occurring L-tryptophan N-glucoside was synthesized using 2-O-pivaloylated glucosyl trichloroacetimidate, which gave beta-N-In-glucosides. From 2-O-acetylated donors only tryptophan-1-yl-ethylidene compounds (amide acetals) were obtained. The employment of alpha-azido L-tryptophan benzyl ester facilitated purification and deprotection and improved the yields of the glycosylation step. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.190