4(R)-benzyl-3-tert-butyl-1,2,3-oxathiazolidine-3,4-dicarboxylate-2,2-dioxide | 1620620-29-2

• 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: 4(R)-benzyl-3-tert-butyl-1,2,3-oxathiazolidine-3,4-dicarboxylate-2,2-dioxide
• 英文别名: benzyl (4R)-3-(tert-butyloxycarbonyl)-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylate；benzyl (4R)-5-t-butoxycarbonyl-1,2,5-sulfamidatecarboxylate；O4-benzyl O3-tert-butyl (4R)-2,2-dioxooxathiazolidine-3,4-dicarboxylate；4-Benzyl 3-(tert-butyl) (R)-1,2,3-oxathiazolidine-3,4-dicarboxylate 2,2-dioxide；4-O-benzyl 3-O-tert-butyl (4R)-2,2-dioxooxathiazolidine-3,4-dicarboxylate
• CAS: 1620620-29-2
• 化学式: C₁₅H₁₉NO₇S
• 分子量: 357.384
• InChiKey: VUNBZHYPHYZUEV-GFCCVEGCSA-N

物化性质

• 沸点：
  451.1±55.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4(R)-benzyl-3-tert-butyl-1,2,3-oxathiazolidine-3,4-dicarboxylate-2,2-dioxide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 以97%的产率得到(4R)-3-(tert-butyloxycarbonyl)-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Stereoselective synthesis of lanthionine derivatives in aqueous solution and their incorporation into the peptidoglycan of Escherichia coli

  摘要：

  The three diastereoisomers-(R,R), (S,S) and meso-of lanthionine were synthesized in aqueous solution with high diastereoselectivity (>99%). The (S) and (R) enantiomers of two differently protected sulfamidates were opened by nucleophilic attack of (R) or (S)-cysteine. Acidification and controlled heating liberated the free lanthionines. Using the same chemistry, an α-benzyl lanthionine was also prepared. The proposed method, which avoids the need of enrichment by recrystallization, opens the way to the labelling of these compounds with (35)S. Furthermore, in vivo bioincorporation into Escherichia coli W7 was studied. No incorporation of α-benzyl lanthionine was observed. In contrast, meso-lanthionine can effectively replace meso-diaminopimelic acid in vivo, while in the presence of (R,R)-lanthionine the initial increase of bacterial growth was followed by cell lysis. In the future, meso-[(35)S]lanthionine could be used to study the biosynthesis of peptidoglycan and its turnover in relation to cell growth and division.

  DOI：

  10.1016/j.bmc.2014.07.023
• 作为产物：
  描述：

  在 吡啶 、 sodium periodate 、 氯化亚砜 、 ruthenium(III) trichloride hydrate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 23.75h， 生成 4(R)-benzyl-3-tert-butyl-1,2,3-oxathiazolidine-3,4-dicarboxylate-2,2-dioxide
  参考文献：
  名称：

  Stereoselective synthesis of lanthionine derivatives in aqueous solution and their incorporation into the peptidoglycan of Escherichia coli

  摘要：

  The three diastereoisomers-(R,R), (S,S) and meso-of lanthionine were synthesized in aqueous solution with high diastereoselectivity (>99%). The (S) and (R) enantiomers of two differently protected sulfamidates were opened by nucleophilic attack of (R) or (S)-cysteine. Acidification and controlled heating liberated the free lanthionines. Using the same chemistry, an α-benzyl lanthionine was also prepared. The proposed method, which avoids the need of enrichment by recrystallization, opens the way to the labelling of these compounds with (35)S. Furthermore, in vivo bioincorporation into Escherichia coli W7 was studied. No incorporation of α-benzyl lanthionine was observed. In contrast, meso-lanthionine can effectively replace meso-diaminopimelic acid in vivo, while in the presence of (R,R)-lanthionine the initial increase of bacterial growth was followed by cell lysis. In the future, meso-[(35)S]lanthionine could be used to study the biosynthesis of peptidoglycan and its turnover in relation to cell growth and division.

  DOI：

  10.1016/j.bmc.2014.07.023

文献信息

• 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。
• 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。
• [EN] MODULATORS OF CYSTIC FIBROSIS TRANSMEMBRANE CONDUCTANCE REGULATOR<br/>[FR] MODULATEURS DU RÉGULATEUR DE LA CONDUCTANCE TRANSMEMBRANAIRE DE LA FIBROSE KYSTIQUE
  申请人：VERTEX PHARMA

  公开号：WO2022076622A2

  公开（公告）日：2022-04-14

  [EN] This disclosure provides modulators of Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) having core structure (I), pharmaceutical compositions containing at least one such modulator, methods of treatment of CFTR mediated diseases, including cystic fibrosis, using such modulators and pharmaceutical compositions, combination pharmaceutical compositions and combination therapies employing those modulators, and processes and intermediates for making such modulators.
  [FR] La présente invention concerne des modulateurs du régulateur de la conductance transmembranaire de la fibrose kystique (RTFK) ayant une structure de coeur (I), des compositions pharmaceutiques contenant au moins un tel modulateur, des procédés de traitement de maladies médiées par le RTFK, y compris la fibrose kystique, à l'aide de tels modulateurs et de telles compositions pharmaceutiques, des compositions pharmaceutiques combinées et des polythérapies utilisant ces modulateurs, ainsi que des procédés et des intermédiaires pour fabriquer de tels modulateurs.
• Stereoselective synthesis of lanthionine derivatives in aqueous solution and their incorporation into the peptidoglycan of Escherichia coli
  作者：Thibaut Denoël、Astrid Zervosen、Thomas Gerards、Christian Lemaire、Bernard Joris、Didier Blanot、André Luxen

  DOI：10.1016/j.bmc.2014.07.023

  日期：2014.9

  The three diastereoisomers-(R,R), (S,S) and meso-of lanthionine were synthesized in aqueous solution with high diastereoselectivity (>99%). The (S) and (R) enantiomers of two differently protected sulfamidates were opened by nucleophilic attack of (R) or (S)-cysteine. Acidification and controlled heating liberated the free lanthionines. Using the same chemistry, an α-benzyl lanthionine was also prepared. The proposed method, which avoids the need of enrichment by recrystallization, opens the way to the labelling of these compounds with (35)S. Furthermore, in vivo bioincorporation into Escherichia coli W7 was studied. No incorporation of α-benzyl lanthionine was observed. In contrast, meso-lanthionine can effectively replace meso-diaminopimelic acid in vivo, while in the presence of (R,R)-lanthionine the initial increase of bacterial growth was followed by cell lysis. In the future, meso-[(35)S]lanthionine could be used to study the biosynthesis of peptidoglycan and its turnover in relation to cell growth and division.