(4S)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxylic acid benzyl ester | 328974-09-0

• 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)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxylic acid benzyl ester
• 英文别名: 2,2-dioxo-1,2,3-oxathiazolidinone-(4S)-carboxylic acid benzyl ester；benzyl (4S)-1,2,5-sulfamidatecarboxylate；benzyl (4S)-2,2-dioxooxathiazolidine-4-carboxylate
• CAS: 328974-09-0
• 化学式: C₁₀H₁₁NO₅S
• 分子量: 257.267
• InChiKey: FUGKUHBXONOJIL-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxylic acid benzyl ester 在 10percent Pd/C 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以100%的产率得到(4S)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxylic acid
  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：

  N-叔丁氧羰基-L-丝氨酸 在 吡啶 、 sodium periodate 、 氯化亚砜 、 rhodium(III) chloride hydrate 作用下， 以 2,2,2-三氟乙醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 28.0h， 生成 (4S)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxylic acid benzyl ester
  参考文献：
  名称：

  O-SUBSTITUTED SERINE DERIVATIVE PRODUCTION METHOD

  摘要：

  发现通过将氨基酸衍生物与环化试剂反应可以生成环状磺胺酸酯。此外，还发现通过将环状磺胺酸酯与醇反应可以产生O-取代的丝氨酸衍生物。

  公开号：

  US20220017456A1

文献信息

• O-SUBSTITUTED SERINE DERIVATIVE PRODUCTION METHOD
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20220017456A1

  公开（公告）日：2022-01-20

  It was discovered that a cyclic sulfamidate can be produced by reacting an amino acid derivative with a cyclization reagent. In addition, it was discovered that an O-substituted serine derivative can be produced by reacting a cyclic sulfamidate with an alcohol.

  发现通过将氨基酸衍生物与环化试剂反应可以生成环状磺胺酸酯。此外，还发现通过将环状磺胺酸酯与醇反应可以产生O-取代的丝氨酸衍生物。
• Synthesis of <i>S</i>-Linked Glycosyl Amino Acids in Aqueous Solution with Unprotected Carbohydrates
  作者：Scott B. Cohen、Randall L. Halcomb

  DOI：10.1021/ol006908b

  日期：2001.2.1

  [GRAPHICS]The cyclic sulfamidate 5 was synthesized in 60% overall yield from L-serine benzyl ester, Compound 5 reacted cleanly with the sodium thiolate salt of a variety of unprotected 1-thio sugars in aqueous buffer to afford the corresponding S-linked amino acid glycoconjugates in good yields after hydrolysis of the N-sulfates.
• Application of Serine- and Threonine-Derived Cyclic Sulfamidates for the Preparation of <i>S</i>-Linked Glycosyl Amino Acids in Solution- and Solid-Phase Peptide Synthesis
  作者：Scott B. Cohen、Randall L. Halcomb

  DOI：10.1021/ja011932l

  日期：2002.3.1

  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.