L-N-2-bromobenzyl-N-methyl-Val-N'-3-(trimethylsilyl)propargyl-Gly-OMe | 503034-72-8

• 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: L-N-2-bromobenzyl-N-methyl-Val-N'-3-(trimethylsilyl)propargyl-Gly-OMe
• 英文别名: methyl 2-[[(2S)-2-[(2-bromophenyl)methyl-methylamino]-3-methylbutanoyl]-(3-trimethylsilylprop-2-ynyl)amino]acetate
• CAS: 503034-72-8
• 化学式: C₂₂H₃₃BrN₂O₃Si
• 分子量: 481.505
• InChiKey: YLWKHXKBALTJFX-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-N-2-bromobenzyl-N-methyl-Val-N'-3-(trimethylsilyl)propargyl-Gly-OMe 在 n-butyl tin hydride 、 偶氮二异丁腈 、 sodium cyanoborohydride 作用下， 以 叔丁醇 为溶剂， 以32%的产率得到(3-isopropyl-2-oxo-4-trimethylsilanylmethyl-2,5-dihydro-pyrrol-1-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Application of Peptidyl Radicals into a New Radical Cascade Leading to Unsaturated γ-Lactams

  摘要：

  Radical cyclization of dipeptides 1a-h proceeds smoothly to give five- and seven-membered rings in good to moderate total yields using Stork's catalytic tin hydride method. A radical is generated on a protecting group and translocated to the peptide moiety. Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group. Encouraging results have notably been obtained with amino acids other than glycine.

  DOI：

  10.1021/jo020602w
• 作为产物：
  描述：

  methyl (2S)-2-[(2-bromophenyl)methylamino]-3-methylbutanoate 在 N-甲基吗啉 、 盐酸 、 sodium cyanoborohydride 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.5h， 生成 L-N-2-bromobenzyl-N-methyl-Val-N'-3-(trimethylsilyl)propargyl-Gly-OMe
  参考文献：
  名称：

  Application of Peptidyl Radicals into a New Radical Cascade Leading to Unsaturated γ-Lactams

  摘要：

  Radical cyclization of dipeptides 1a-h proceeds smoothly to give five- and seven-membered rings in good to moderate total yields using Stork's catalytic tin hydride method. A radical is generated on a protecting group and translocated to the peptide moiety. Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group. Encouraging results have notably been obtained with amino acids other than glycine.

  DOI：

  10.1021/jo020602w

文献信息

• Application of Peptidyl Radicals into a New Radical Cascade Leading to Unsaturated γ-Lactams
  作者：Robert Andrukiewicz、Rafał Loska、Vladimir Prisyahnyuk、Krzysztof Staliński

  DOI：10.1021/jo020602w

  日期：2003.2.1

  Radical cyclization of dipeptides 1a-h proceeds smoothly to give five- and seven-membered rings in good to moderate total yields using Stork's catalytic tin hydride method. A radical is generated on a protecting group and translocated to the peptide moiety. Following a cyclization reaction, the vinyl radical can abstract hydrogen from a benzyl group on an amine, which results in elimination of the protected amine group. Encouraging results have notably been obtained with amino acids other than glycine.