(4S)-N-(p-methoxybenzyl)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxylic acid | 415919-24-3

• 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-carboxylic acid
• 英文别名: (4S)-N-(p-methoxybenzyl)-2,2-dioxo-1,2,3-oxathiazolidione-4-carboxylic acid；(4S)-3-[(4-methoxyphenyl)methyl]-2,2-dioxooxathiazolidine-4-carboxylic acid
• CAS: 415919-24-3
• 化学式: C₁₁H₁₃NO₆S
• 分子量: 287.293
• InChiKey: JUVUHHZHKFNFOF-JTQLQIEISA-N

物化性质

• 沸点：
  500.7±60.0 °C(Predicted)
• 密度：
  1.496±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-叔丁基苯酚 、 (4S)-N-(p-methoxybenzyl)-2,2-dioxo-1,2,3-oxathiazolidinone-4-carboxylic acid 在 sodium hydride 、 sodium hydrogen sulfate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 7.08h， 以54%的产率得到(S)-3-(3-(tert-butyl)phenoxy)-2-((4-methoxybenzyl)amino)propanoic acid
  参考文献：
  名称：

  Efficient asymmetric synthesis of N-protected-β-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid

  摘要：

  发展了一种首个区域选择性的丝氨酸衍生环状硫酰胺在强亲核试剂（如ArONa）作用下开环的方法，其中通过羧酸根阴离子的电子效应反转克服了强亲核试剂对丝氨酸硫酰胺酯的β-消除反应。该方法提供了便捷和直接获取多种N-Boc和N-PMB保护的β-芳氧-α-氨基酸，且具有完全的对映体纯度保留，产率中等到高。

  DOI：

  10.1039/c4ob01047g
• 作为产物：
  描述：

  在 10percent Pd/C ruthenium trichloride 、 sodium periodate 、 氢气 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 3.25h， 生成 (4S)-N-(p-methoxybenzyl)-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

文献信息

• Enantiopure synthesis of dihydrobenzo[1,4]-oxazine-3-carboxylic acids and a route to benzoxazinyl oxazolidinones
  作者：Rajesh Malhotra、Tushar K. Dey、Sourav Basu、Saumen Hajra

  DOI：10.1039/c4ob02475c

  日期：——

  A two step protocol is developed for the enantiopure synthesis of dihydrobenzoxazine-3-carboxylic acids via RuPhos Palladacycle-catalyzed aminoarylation of β-(2-bromoaryloxy)amino acids.

  已开发出一个两步协议，用于通过RuPhos Palladacycle催化的氨基芳基化反应合成对映纯的二氢苯并噁嗪-3-羧酸，其中底物为β-(2-溴芳氧基)氨基酸。
• Efficient asymmetric synthesis of N-protected-β-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid
  作者：Rajesh Malhotra、Tushar K. Dey、Swarup Dutta、Sourav Basu、Saumen Hajra

  DOI：10.1039/c4ob01047g

  日期：——

  First regioselective ring opening of serine derived cyclic sulfamidate by hard nucleophiles like ArONa is developed, where β-elimination of serine sulfamidate ester by stronger nucleophiles is overcome by reversal of the electronic effect of the carboxylate anion. This method provides easy and direct access to a variety of N-Boc- and N-PMB protected β-aryloxy-α-amino acids with complete retention of enantiopurity in moderate to high yields.

  发展了一种首个区域选择性的丝氨酸衍生环状硫酰胺在强亲核试剂（如ArONa）作用下开环的方法，其中通过羧酸根阴离子的电子效应反转克服了强亲核试剂对丝氨酸硫酰胺酯的β-消除反应。该方法提供了便捷和直接获取多种N-Boc和N-PMB保护的β-芳氧-α-氨基酸，且具有完全的对映体纯度保留，产率中等到高。
• 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.