(3S)-3-[[(R)-hydroxy-(2S,4R)-(N-tert-butoxycarbonyl-4-methanesulfonyloxy) pyrrolidin-2-yl]methyl]pyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (3S)-3-[[(R)-hydroxy-(2S,4R)-(N-tert-butoxycarbonyl-4-methanesulfonyloxy) pyrrolidin-2-yl]methyl]pyrrolidin-2-one
• 英文别名: tert-butyl (2S,4R)-2-hydroxy-4-methylsulfonyloxy-2-[[(3S)-2-oxopyrrolidin-3-yl]methyl]pyrrolidine-1-carboxylate
• 化学式: C₁₅H₂₆N₂O₇S
• 分子量: 378.447
• InChiKey: HJHONBZDYGDXGK-RWSFTLGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-二甲氨基吡啶 、 (3S)-3-[[(R)-hydroxy-(2S,4R)-(N-tert-butoxycarbonyl-4-methanesulfonyloxy) pyrrolidin-2-yl]methyl]pyrrolidin-2-one 、 二碳酸二叔丁酯 在 ammonium chloride 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 (3S)-N-tert-butoxycarbonyl-3-[[(R)-hydroxy-(2S,4R)-(N-tert-butoxycarbonyl-4-methanesulfonyloxy)pyrrolidin-2-yl]methyl]pyrrolidin-2-one
  参考文献：
  名称：

  Intermediates useful for the manufacture of carbapenem and a stereoselective manufacturing method therefor

  摘要：

  本发明提供了一种高效的立体选择性方法，用于制造（2S,4S）-2-[(R)-羟基-(3R)-环胺-3-基]甲基吡咯烷-4-硫醇或其盐，该化合物可用作头孢烯类抗生素的

  公开号：

  US06218550B1

文献信息

• INTERMEDIATES USEFUL IN PRODUCING CARBAPENEM AND PROCESS FOR THE STEREOSELECTIVE PRODUCTION OF THE SAME
  申请人：Eisai Co., Ltd.

  公开号：EP1020440A1

  公开（公告）日：2000-07-19

  An efficient process for the stereoselective production of (2S,4S)-2-[[(R)-hydroxy-(3R)-cyclic amin-3-yl]methyl]pyrrolidine-4-thiol or its salts, which are intermediates useful in producing carbapenem, by reacting a compound represented by general formula (I) (wherein R1 represents lower alkylsulfonyl, optionally substituted arylsulfonyl or alkylsilyl; and R2 represents an amino-protective group) with a compound represented by general formula (II), wherein R3 represents optionally substituted lower alkyl or aryl; X represents oxygen or sulfur; Y represents azido or nitro; and m is an integer of from 2 to 5.

  一种立体选择性生产(2S,4S)-2-[[(R)-羟基-(3R)-环氨基-3-基]甲基]吡咯烷-4-硫醇或其盐的高效工艺，它们是用于生产碳青霉烯的中间体，其方法是使通式(I)代表的化合物（其中R1代表低级烷基磺酰基、任选取代的芳基磺酰基或烷基硅基，R2代表氨基保护基团）与通式(II)代表的化合物反应，其中R3代表任选取代的低级烷基或芳基；X代表氧或硫；Y代表叠氮基；其中 R3 代表任选取代的低级烷基或芳基；X 代表氧或硫；Y 代表叠氮或硝基；m 为 2 至 5 的整数。
• US6372914B1
  申请人：——

  公开号：US6372914B1

  公开（公告）日：2002-04-16
• Intermediates useful for the manufacture of carbapenem and a stereoselective manufacturing method therefor
  申请人：Eisai Co., Ltd.

  公开号：US06218550B1

  公开（公告）日：2001-04-17

  The present invention provides an efficient stereoselective method for manufacturing (2S,4S)-2-[[(R)-hydroxy-(3R)-cyclic amine-3-yl]methyl]pyrrolidine-4-thiol or a salt thereof which is useful as an intermediate for the manufacture of carbapenem and also provides the intermediate. A method for manufacturing which comprises the step of reacting a compound of the formula (I): (wherein, R1 is a lower alkylsulfonyl group, an optionally substituted arylsulfonyl group or an alkylsilyl group; and R2 is a protecting group for an amino group) with a compound of the formula (II): (wherein, R3 is a substituted or unsubstituted lower alkyl group or aryl group; X is an oxygen atom or a sulfur atom; Y is an azide group or a nitro group; and m is an integer of 2 to 5).

  本发明提供了一种高效的立体选择性方法，用于制造（2S,4S）-2-[(R)-羟基-(3R)-环胺-3-基]甲基吡咯烷-4-硫醇或其盐，该化合物可用作头孢烯类抗生素的