Sodium 5R,6S-6-(1R-Hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio)-2-penem-3-carboxylate | 112294-81-2

• 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: Sodium 5R,6S-6-(1R-Hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio)-2-penem-3-carboxylate
• 英文别名: Sodium 5R,6S-6-(1R-Hydroxyethyl)-2-[(1R-oxo-3S-thiolanyl) thio]penem-3-carboxylate；Sulopenem sodium；sodium;(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(1R,3S)-1-oxothiolan-3-yl]sulfanyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
• CAS: 112294-81-2
• 化学式: C₁₂H₁₄NO₅S₃*Na
• 分子量: 371.435
• InChiKey: MRHMJKHFABHUKB-LQUSNCHHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.92
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Sodium 5R,6S-6-(1R-Hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio)-2-penem-3-carboxylate 生成 硫培南
  参考文献：
  名称：

  VOLKMANN, ROBERT A.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Chloroallyl (5R,6S)-6-(1(R)-hydroxyethyl)-2-<(1(R)-oxo-3(S)-thiolanyl)thio>-2-penem-3-carboxylate 生成 Sodium 5R,6S-6-(1R-Hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio)-2-penem-3-carboxylate
  参考文献：
  名称：

  VOLKMANN, R. A.;LINDNER, D. L.

  摘要：

  DOI：

文献信息

• Process for the preparation of penems
  申请人：Pfizer Inc.

  公开号：US04895940A1

  公开（公告）日：1990-01-23

  An efficient, multistep process for the synthesis of 6-(1-hydroxyethyl) 2-thio-substituted penem antibiotics from 2-[4R-(triphenylmethy lthio)-3S-(1S-(dimethyl-t-butylsilyloxy)ethyl)-2-azetidon-1-yl]acetic acid esters.

  一个高效的多步骤过程，用于从2-[4R-(三苯甲基硫基)-3S-(1S-(二甲基-叔丁基硅氧基)乙基)-2-氮杂环丁-1-基]乙酸酯合成6-(1-羟基乙基)2-硫代取代的青霉烯抗生素。
• Penem derivatives
  申请人：Pfizer Inc.

  公开号：US04992543A1

  公开（公告）日：1991-02-12

  An efficient, multistep process for the synthesis of certain 6-(1-hydroxyethyl) 2-substituted penem antibiotics from 2-[4R-(triphenylmethylthio)-3S-(1R-(dimethyl-t-butylsilyloxy)ethyl)-2-azet idon-1 yl]acetic acid ester.

  一种高效的多步骤过程，用于从2-[4R-(三苯甲基硫基)-3S-(1R-(二甲基-叔丁基硅氧基)乙基)-2-氮杂环丁-1-基]乙酸酯合成某些6-(1-羟基乙基)2-取代的青霉烯类抗生素。
• Process for optically active 3-(methane-sulfonyloxy)thiolane and analogs
  申请人：Pfizer Inc.

  公开号：US04874877A1

  公开（公告）日：1989-10-17

  Intermediates and a stepwise process for the conversion of D-methionine or certain of its derivatives to optically active compounds of the formula ##STR1## wherein R is (C.sub.1 -C.sub.3) alkyl, phenyl or tolyl. The latter compounds are in turn useful as an intermediate in the preparation of penem antibiotic 5R,6S-6-(1R-hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio)-2-penem-3-carboxylic acid and corresponding pharmaceutically acceptable salts and esters.

  D-蛋氨酸或其某些衍生物转化为光学活性化合物的中间体及逐步过程，其中R为C1-C3烷基，苯基或甲苯基。这些化合物又作为制备青霉烯抗生素5R，6S-6-(1R-羟基乙基)-2-(1R-氧代-3S-巯基乙烷硫基)-2-青霉烯-3-羧酸及其相应的药用可接受盐和酯的中间体。
• Diastereomeric
  申请人：Pfizer Inc.

  公开号：US05013729A1

  公开（公告）日：1991-05-07

  Diastereomeric 5R,6S-6-(1R-hydroxyethyl)-2-(1S-oxo-3R-thiolanylthio)-2-penem-3-carboxylic acid and 5R,6S-6-(1R-hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio )-2-penem-3-carboxylic acid, and pharmaceutically-acceptable salts and in vivo hydrolyzable esters thereof, useful as systemic antibacterial agents; and intermediates and processes which are useful in the said synthesis of said diastereoisomers.

  对映异构体 5R,6S-6-(1R-羟基乙基)-2-(1S-氧代-3R-巯基丙基硫代)-2-氧杂-3-羧酸和 5R,6S-6-(1R-羟基乙基)-2-(1R-氧代-3S-巯基丙基硫代)-2-氧杂-3-羧酸，以及它们的药用可接受盐和体内可水解酯，作为全身用抗菌剂是有用的；以及用于所述对映异构体合成的中间体和过程。
• Process for removal of allyl group or allyloxycarbonyl group
  申请人：Pfizer Inc.

  公开号：US05621084A1

  公开（公告）日：1997-04-15

  This invention relates to a process for the removal of an allyl or allyloxycarbonyl group from an allyl or allyloxycarbonyl group protected compound (such as an allylic ester, carbonate, carbamate, O-allyl derivatives or N-allyl derivatives), which comprises contacting the allyl or allyloxycarbonyl group protected compound with a sulfinic acid compound, in the presence of a palladium catalyst in a reaction-inert solvent. Preferably, the sulfinic acid compound is represented by the formula: X--SO.sub.2 M (I) wherein X is C.sub.1-20 alkyl, substituted C.sub.1-20 alkyl (wherein the substituent(s) are independently halo, nitro, sulfo, oxo, amino, cyano, carboxy, hydroxy or moieties derived therefrom), phenyl, substituted phenyl (wherein the substituent(s) are independently C.sub.1-3 alkyl, halo nitro, sulfo, oxo, amino, cyano, carboxy, hydroxy, acetamido or moieties derived therefrom), furyl or thienyl; and M is hydrogen, an alkali metal or ammonium salt residue. Of these, most preferred sulfinic acid compound is lithium p-toluenesulfinate, sodium p-toluenesulfinate, potassium p-toluenesulfinate, p-toluenesulfinic acid, ammonium p-toluenesulfinate, lithium benzenesulfinate, sodium benzenesulfinate, potassium benzenesulfinate, benzenesulfinic acid or ammonium benzenesulfinate. This invention is well suited to a process for the conversion of an allyl ester of 5R,6S-6-(1R-hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio)-2-penem-3-carboxylic acid to 5R,6S-6-(1R-hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio)-2-penem-3-carboxylic acid.

  本发明涉及一种从烯丙基或烯丙氧羰基保护的化合物（如烯丙基酯、碳酸酯、氨基甲酸酯、O-烯丙基衍生物或N-烯丙基衍生物）中去除烯丙基或烯丙氧羰基基团的方法，该方法包括在钯催化剂存在下，在反应惰性溶剂中使烯丙基或烯丙氧羰基保护的化合物与亚磺酸化合物接触。优选地，亚磺酸化合物具有以下通式：X--SO₂M（I），其中X为C₁-₂₀烷基、取代的C₁-₂₀烷基（其中取代基独立地为卤素、硝基、磺基、氧代、氨基、氰基、羧基、羟基或由此衍生的基团）、苯基、取代的苯基（其中取代基独立地为C₁-₃烷基、卤素、硝基、磺基、氧代、氨基、氰基、羧基、羟基、乙酰氨基或由此衍生的基团）、呋喃基或噻吩基；M为氢、碱金属或铵盐残基。在这些亚磺酸化合物中，最优选的是对甲苯亚磺酸锂、对甲苯亚磺酸钠、对甲苯亚磺酸钾、对甲苯亚磺酸、对甲苯亚磺酸铵、苯亚磺酸锂、苯亚磺酸钠、苯亚磺酸钾、苯亚磺酸或苯亚磺酸铵。本发明特别适用于将5R,6S-6-(1R-羟乙基)-2-(1R-氧代-3S-噻烷硫基)-2-青霉烯-3-羧酸的烯丙基酯转化为5R,6S-6-(1R-羟乙基)-2-(1R-氧代-3S-噻烷硫基)-2-青霉烯-3-羧酸的过程。