N-acetyl-4-bromo-N-(tert-butoxycarbonyl)-1-tosyl-D-tryptophan methyl ester | 343846-39-9

• 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: N-acetyl-4-bromo-N-(tert-butoxycarbonyl)-1-tosyl-D-tryptophan methyl ester
• 英文别名: methyl (2R)-2-[acetyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-[4-bromo-1-(4-methylphenyl)sulfonylindol-3-yl]propanoate
• CAS: 343846-39-9
• 化学式: C₂₆H₂₉BrN₂O₇S
• 分子量: 593.495
• InChiKey: QTKZJAZQVXNVKL-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-acetyl-4-bromo-N-(tert-butoxycarbonyl)-1-tosyl-D-tryptophan methyl ester 在 氢氧化钾 、 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 水 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 50.5h， 生成 N-(tert-butoxycarbonyl)-4-bromo-N-methyl-1-tosyl-D-tryptophan methyl ester
  参考文献：
  名称：

  An Efficient Method of Synthesizing Optically Pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan Methyl Ester, a Key Intermediate in the Synthesis of Optically Active Ergot Alkaloids

  摘要：

  Optically pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan methyl ester (D-4), a key intermediate in the synthesis of optically active ergot alkaloids such as chanoclavine-I (7) and costaclavine (8), was prepared from N-acetyl-4-bromo-D-tryptophan (D-ll) obtained from 4-bromoindole (9) and DL-serine (10) in two steps.

  DOI：

  10.3987/com-00-9137
• 作为产物：
  描述：

  4-溴吲哚 在 4-二甲氨基吡啶 、 sodium hydroxide 、 acylase from Aspergillus genus 、 十六烷基三甲基溴化铵 、 cobalt(II) chloride 作用下， 以 四氢呋喃 、 phosphate buffer 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 61.0h， 生成 N-acetyl-4-bromo-N-(tert-butoxycarbonyl)-1-tosyl-D-tryptophan methyl ester
  参考文献：
  名称：

  An Efficient Method of Synthesizing Optically Pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan Methyl Ester, a Key Intermediate in the Synthesis of Optically Active Ergot Alkaloids

  摘要：

  Optically pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan methyl ester (D-4), a key intermediate in the synthesis of optically active ergot alkaloids such as chanoclavine-I (7) and costaclavine (8), was prepared from N-acetyl-4-bromo-D-tryptophan (D-ll) obtained from 4-bromoindole (9) and DL-serine (10) in two steps.

  DOI：

  10.3987/com-00-9137

文献信息

• An Efficient Method of Synthesizing Optically Pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan Methyl Ester, a Key Intermediate in the Synthesis of Optically Active Ergot Alkaloids
  作者：Yuusaku Yokoyama、Kumi Osanai、Masaharu Mitsuhashi、Kazuhiro Kondo、Yasuoki Murakami

  DOI：10.3987/com-00-9137

  日期：——

  Optically pure N-Boc-4-bromo-N-methyl-1-tosyl-D-tryptophan methyl ester (D-4), a key intermediate in the synthesis of optically active ergot alkaloids such as chanoclavine-I (7) and costaclavine (8), was prepared from N-acetyl-4-bromo-D-tryptophan (D-ll) obtained from 4-bromoindole (9) and DL-serine (10) in two steps.