(1S,3S,1'R,2'S)-1-[1'-[(N-benzyloxycarbonyl)amino]-2'-methyl-butyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester | 1009587-65-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (1S,3S,1'R,2'S)-1-[1'-[(N-benzyloxycarbonyl)amino]-2'-methyl-butyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester
• 英文别名: methyl (1S,3S)-1-[(1R,2S)-2-methyl-1-(phenylmethoxycarbonylamino)butyl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1009587-65-8
• 化学式: C₂₆H₃₁N₃O₄
• 分子量: 449.55
• InChiKey: MYZOPKFYXJUQMX-UDGMGYNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-色氨酸甲酯 、 benzyl N-[(2R,3S)-3-methyl-1-oxopentan-2-yl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到(1S,3S,1'R,2'S)-1-[1'-[(N-benzyloxycarbonyl)amino]-2'-methyl-butyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Diastereoselective Pictet–Spengler condensation of tryptophan with α-amino aldehydes as chiral carbonyl components

  摘要：

  The Pictet-Spengler reaction of Trp with alpha-amino aldehydes derived from L and D-amino acids was studied in terms of double stereodifferentiation. The results observed for D-amino aldehydes represent 'matched' situation (one diastereoisomer was formed) whereas with L-amino aldehydes 'mismatched' (two diastereoisomers were formed). The conformation of newly formed six-membered ring was analyzed. It was found that stable conformers were different for cis and trans isomers. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.037

文献信息

• Diastereoselective Pictet–Spengler condensation of tryptophan with α-amino aldehydes as chiral carbonyl components
  作者：Karolina Pulka、Piotr Kulis、Dagmara Tymecka、Lukasz Frankiewicz、Marcin Wilczek、Wiktor Kozminski、Aleksandra Misicka

  DOI：10.1016/j.tet.2007.11.037

  日期：2008.2

  The Pictet-Spengler reaction of Trp with alpha-amino aldehydes derived from L and D-amino acids was studied in terms of double stereodifferentiation. The results observed for D-amino aldehydes represent 'matched' situation (one diastereoisomer was formed) whereas with L-amino aldehydes 'mismatched' (two diastereoisomers were formed). The conformation of newly formed six-membered ring was analyzed. It was found that stable conformers were different for cis and trans isomers. (c) 2007 Elsevier Ltd. All rights reserved.