(R)-N-acetyl-4-bromo-1-tosyltryptophan methyl ester | 343846-38-8

• 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: (R)-N-acetyl-4-bromo-1-tosyltryptophan methyl ester
• 英文别名: N-acetyl-4-bromo-1-tosyl-D-tryptophan methyl ester；methyl (2R)-2-acetamido-3-[4-bromo-1-(4-methylphenyl)sulfonylindol-3-yl]propanoate
• CAS: 343846-38-8
• 化学式: C₂₁H₂₁BrN₂O₅S
• 分子量: 493.378
• InChiKey: JLJXHTLNBUBEAU-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-N-acetyl-4-bromo-1-tosyltryptophan methyl ester 在 4-二甲氨基吡啶 、 氢氧化钾 、 一水合肼 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 51.5h， 生成 (2R)-3-[4-bromo-1-(4-methylphenyl)sulfonylindol-3-yl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
  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：

  N-acetyl-4-bromo-DL-tryptophan 在 sodium hydroxide 、 acylase from Aspergillus genus 、 十六烷基三甲基溴化铵 、 cobalt(II) chloride 作用下， 以 phosphate buffer 、 1,2-二氯乙烷 为溶剂， 反应 55.5h， 生成 (R)-N-acetyl-4-bromo-1-tosyltryptophan 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 Improved Synthesis of Optically Pure (R)-4-Bromo-N-methyl-1-tosyltryptophan Derivative, a Key Intermediate in the Synthesis of Ergot Alkaloids
  作者：Yuusaku Yokoyama、Ryoko Hara、Nahoko Kato、Yasuoki Murakami、Hiroaki Okuno

  DOI：10.3987/com-05-10380

  日期：——

  Optically pure (R)-N-Boc- or (R)-Cbz-4-bromo-N-methyl-1-tosyltryptophan methyl ester (11a or b) was synthesized in 2 steps from (R)-N-acetyl-4-bromo-1-tosyltryptophan methyl ester (7) by simultaneous N-methylation and deacetylation using methyl trifluoromethanesulfonate (TfOMe) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP).
• 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.