N¹-(β-D-glucopyranosyl-⁴C₁)-L-tryptophan

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: N¹-(β-D-glucopyranosyl-⁴C₁)-L-tryptophan
• 英文别名: tryptophan N-glucoside；(2S)-2-amino-3-[1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indol-3-yl]propanoic acid
• 化学式: C₁₇H₂₂N₂O₇
• 分子量: 366.371
• InChiKey: ZHBHZDMTVVJASV-JOSVURMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl glucopyranose 在 吡啶 、 palladium(II) oxide 、 三氟甲磺酸三甲基硅酯 、 氢气 、 乙酸肼 、 甲胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 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

文献信息

• Synthesis of tryptophan N -glucoside
  作者：Melanie Schnabel、Birgit Römpp、Daniel Ruckdeschel、Carlo Unverzagt

  DOI：10.1016/j.tetlet.2003.10.190

  日期：2004.1

  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.