ethyl N-(benzyloxycarbonyl)-D-tryptophanylglycinate | 264236-33-1

• 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: ethyl N-(benzyloxycarbonyl)-D-tryptophanylglycinate
• 英文别名: ethyl 2-[[(2R)-3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoyl]amino]acetate
• CAS: 264236-33-1
• 化学式: C₂₃H₂₅N₃O₅
• 分子量: 423.469
• InChiKey: ATGRSTQNQQGELS-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl N-(benzyloxycarbonyl)-D-tryptophanylglycinate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 sodium hydroxide 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 42.0h， 生成 (3R)-1-acetyl-4-(o-azidobenzoyl)-3-(1-acetyl-3-indolylmethyl)-2,5-piperazinedione
  参考文献：
  名称：

  A New Route toward 4-Substituted Pyrazino[2,1-b]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine

  摘要：

  Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.

  DOI：

  10.1021/jo991626e
• 作为产物：
  描述：

  甘氨酸乙酯盐酸盐 、 N-苄氧羰基-D-色氨酸 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以65%的产率得到ethyl N-(benzyloxycarbonyl)-D-tryptophanylglycinate
  参考文献：
  名称：

  A New Route toward 4-Substituted Pyrazino[2,1-b]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine

  摘要：

  Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.

  DOI：

  10.1021/jo991626e

文献信息

• A New Route toward 4-Substituted Pyrazino[2,1-<i>b</i>]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine
  作者：Pilar Cledera、Carmen Avendaño、J. Carlos Menéndez

  DOI：10.1021/jo991626e

  日期：2000.3.1

  Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.