(4S)-N-(p-methoxybenzyl)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxyl-leucine benzyl ester | 415919-25-4

• 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: (4S)-N-(p-methoxybenzyl)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxyl-leucine benzyl ester
• 英文别名: benzyl (2S)-2-[[(4S)-3-[(4-methoxyphenyl)methyl]-2,2-dioxooxathiazolidine-4-carbonyl]amino]-4-methylpentanoate
• CAS: 415919-25-4
• 化学式: C₂₄H₃₀N₂O₇S
• 分子量: 490.577
• InChiKey: RVXUKQDRJAIBJR-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4S)-N-(p-methoxybenzyl)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxyl-leucine benzyl ester 在 10percent Pd/C ammonium cerium(IV) nitrate 、 氢气 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 (4S)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxyl-leucine
  参考文献：
  名称：

  Application of Serine- and Threonine-Derived Cyclic Sulfamidates for the Preparation of S-Linked Glycosyl Amino Acids in Solution- and Solid-Phase Peptide Synthesis

  摘要：

  Cyclic sulfamidates were synthesized in 60% yield from L-serine and allo-L-threonine, respectively. These sulfamidates reacted with a variety of unprotected 1-thio sugars in aqueous bicarbonate buffer (pH 8) to afford the corresponding S-linked serine- and threonine-glycosyl amino acids with good diastereo-selectivity (greater than or equal to97%) after hydrolysis of the A sulfates. The serine-derived sulfamidate was incorporated into a simple dlipeptide to generate a reactive dipeptide substrate that underwent chemoselective ligation with a 1-thio sugar to afford an S-linked glycopeptide. This sulfamidate was also incorporated into a peptide on a solid support in conjunction with solid-phase peptide synthesis. Chemoselective ligation of a 1-thio sugar with the cyclic sulfamidate was achieved on the solid support, followed by removal of the N-sulfate. Finally, the peptide chain of the resulting support-bound S-linked glycopeptide was extended using standard peptide synthesis procedures.

  DOI：

  10.1021/ja011932l
• 作为产物：
  描述：

  (4S)-N-(p-methoxybenzyl)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxylic acid benzyl ester 在 10percent Pd/C N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.08h， 生成 (4S)-N-(p-methoxybenzyl)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxyl-leucine benzyl ester
  参考文献：
  名称：

  Application of Serine- and Threonine-Derived Cyclic Sulfamidates for the Preparation of S-Linked Glycosyl Amino Acids in Solution- and Solid-Phase Peptide Synthesis

  摘要：

  Cyclic sulfamidates were synthesized in 60% yield from L-serine and allo-L-threonine, respectively. These sulfamidates reacted with a variety of unprotected 1-thio sugars in aqueous bicarbonate buffer (pH 8) to afford the corresponding S-linked serine- and threonine-glycosyl amino acids with good diastereo-selectivity (greater than or equal to97%) after hydrolysis of the A sulfates. The serine-derived sulfamidate was incorporated into a simple dlipeptide to generate a reactive dipeptide substrate that underwent chemoselective ligation with a 1-thio sugar to afford an S-linked glycopeptide. This sulfamidate was also incorporated into a peptide on a solid support in conjunction with solid-phase peptide synthesis. Chemoselective ligation of a 1-thio sugar with the cyclic sulfamidate was achieved on the solid support, followed by removal of the N-sulfate. Finally, the peptide chain of the resulting support-bound S-linked glycopeptide was extended using standard peptide synthesis procedures.

  DOI：

  10.1021/ja011932l