(4R)-3-(tert-butyloxycarbonyl)-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylic acid | 1621706-88-4

• 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: (4R)-3-(tert-butyloxycarbonyl)-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylic acid
• 英文别名: 3(R)-(tert-butoxycarbonyl)-1,2,3-oxathiazolidine-4-carboxylicacid-2,2-dioxide
• CAS: 1621706-88-4
• 化学式: C₈H₁₃NO₇S
• 分子量: 267.26
• InChiKey: PTDHBPUFDVFTCC-RXMQYKEDSA-N

物化性质

• 沸点：
  404.2±55.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  110.21
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R)-3-(tert-butyloxycarbonyl)-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylic acid 在 sodium tetrahydroborate 、 chloro-(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1‘-biphenyl)[2-(2-aminoethyl)phenyl] palladium(ll) methyl-tert-butyl ether adduct 、 sodium hydride 、 caesium carbonate 、 二异丙胺 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 mineral oil 为溶剂， 反应 22.5h， 生成
  参考文献：
  名称：

  Enantiopure synthesis of dihydrobenzo[1,4]-oxazine-3-carboxylic acids and a route to benzoxazinyl oxazolidinones

  摘要：

  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。

  DOI：

  10.1039/c4ob02475c
• 作为产物：
  描述：

  benzyl (4R)-5-t-butoxycarbonyl-1,2,5-sulfamiditecarboxylate 在 sodium periodate 、 ruthenium(III) trichloride hydrate 、 palladium 10% on activated carbon 、 氢气 作用下， 以 水 、 乙酸乙酯 、 乙腈 为溶剂， 20.0 ℃ 、482.64 kPa 条件下， 反应 12.25h， 生成 (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

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。
• Asymmetric synthesis towards doxanthrine, a dopamine D1 full agonist
  作者：Rajesh Malhotra、Amit Ghosh、Swarup Dutta、Tushar K. Dey、Sourav Basu、Saumen Hajra

  DOI：10.1039/c4ra06617k

  日期：——

  First asymmetric synthesis of towards doxanthrine is accomplished with high diastereo- and enantioselectivity from β-aryloxyamino acid derived from D-serine.

  使用D-丝氨酸衍生的β-芳氧氨基酸成功实现了朝向多黄嗪的首个不对称合成，具有高的对映异构体选择性和对映体选择性。