S-(2,4,6-Trimethoxybenzyl)-L-cysteine | 140835-58-1

• 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: S-(2,4,6-Trimethoxybenzyl)-L-cysteine
• 英文别名: (2R)-2-amino-3-[(2,4,6-trimethoxyphenyl)methylsulfanyl]propanoic acid
• CAS: 140835-58-1
• 化学式: C₁₃H₁₉NO₅S
• 分子量: 301.364
• InChiKey: HJZAATQHLMQOKU-JTQLQIEISA-N

物化性质

• 沸点：
  476.6±45.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl azidoformate 、 S-(2,4,6-Trimethoxybenzyl)-L-cysteine 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以76%的产率得到N^α-(9-Fluorenylmethyloxycarbonyl)-S-(2,4,6-trimethoxybenzyl)-L-cysteine
  参考文献：
  名称：

  S-2,4,6-trimethoxybenzyl (Tmob): a novel cysteine protecting group for the N.alpha.-(9-fluorenylmethoxycarbonyl) (Fmoc) strategy of peptide synthesis

  摘要：

  The S-2,4,6-trimethoxybenzyl (Tmob) group can be introduced onto sulfhydryl functions from the corresponding alcohol, with acid catalysis, and is in turn removed rapidly by treatment with 30% trifluoroacetic acid-dichloromethane in the presence of phenol, thioanisole, and water (5% each) or 6% trifluoroacetic acid-dichloromethane in the presence of triethylsilane or triisopropylsilane (0.5%). The appropriate cysteine derivative was prepared and applied with other N(alpha)-Fmoc protected amino acids to the solid-phase syntheses of several model peptides. Acidolytic deblocking in the presence of cation scavengers and reducing agents gave the free thiol, whereas oxidative deblocking with iodine or thallium(III) trifluoroacetate provided an intramolecular disulfide. The chemistry of the S-Tmob group compares favorably to established chemistries with the acid-labile and oxidizable S-triphenylmethyl (trityl, Trt) group, as well as with the oxidizable S-acetamidomethyl (Acm) group.

  DOI：

  10.1021/jo00037a013
• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲醛 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成 S-(2,4,6-Trimethoxybenzyl)-L-cysteine
  参考文献：
  名称：

  S-2,4,6-trimethoxybenzyl (Tmob): a novel cysteine protecting group for the N.alpha.-(9-fluorenylmethoxycarbonyl) (Fmoc) strategy of peptide synthesis

  摘要：

  The S-2,4,6-trimethoxybenzyl (Tmob) group can be introduced onto sulfhydryl functions from the corresponding alcohol, with acid catalysis, and is in turn removed rapidly by treatment with 30% trifluoroacetic acid-dichloromethane in the presence of phenol, thioanisole, and water (5% each) or 6% trifluoroacetic acid-dichloromethane in the presence of triethylsilane or triisopropylsilane (0.5%). The appropriate cysteine derivative was prepared and applied with other N(alpha)-Fmoc protected amino acids to the solid-phase syntheses of several model peptides. Acidolytic deblocking in the presence of cation scavengers and reducing agents gave the free thiol, whereas oxidative deblocking with iodine or thallium(III) trifluoroacetate provided an intramolecular disulfide. The chemistry of the S-Tmob group compares favorably to established chemistries with the acid-labile and oxidizable S-triphenylmethyl (trityl, Trt) group, as well as with the oxidizable S-acetamidomethyl (Acm) group.

  DOI：

  10.1021/jo00037a013

文献信息

• S-2,4,6-trimethoxybenzyl (Tmob): a novel cysteine protecting group for the N.alpha.-(9-fluorenylmethoxycarbonyl) (Fmoc) strategy of peptide synthesis
  作者：Mark C. Munson、Carlos Garcia-Echeverria、Fernando Albericio、George Barany

  DOI：10.1021/jo00037a013

  日期：1992.5

  The S-2,4,6-trimethoxybenzyl (Tmob) group can be introduced onto sulfhydryl functions from the corresponding alcohol, with acid catalysis, and is in turn removed rapidly by treatment with 30% trifluoroacetic acid-dichloromethane in the presence of phenol, thioanisole, and water (5% each) or 6% trifluoroacetic acid-dichloromethane in the presence of triethylsilane or triisopropylsilane (0.5%). The appropriate cysteine derivative was prepared and applied with other N(alpha)-Fmoc protected amino acids to the solid-phase syntheses of several model peptides. Acidolytic deblocking in the presence of cation scavengers and reducing agents gave the free thiol, whereas oxidative deblocking with iodine or thallium(III) trifluoroacetate provided an intramolecular disulfide. The chemistry of the S-Tmob group compares favorably to established chemistries with the acid-labile and oxidizable S-triphenylmethyl (trityl, Trt) group, as well as with the oxidizable S-acetamidomethyl (Acm) group.