(4S,5R)-4-benzyl-5-hydroxymethyloxazolidin-2-one | 157668-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,5R)-4-benzyl-5-hydroxymethyloxazolidin-2-one
• 英文别名: (4S,5R)-5-hydroxymethyl-4-phenylmethyloxazolidin-2-one；(4S,5R)-4-benzyl-5-(hydroxymethyl)-1,3-oxazolidin-2-one
• CAS: 157668-56-9
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: FXOAAIKBXQDDOK-UWVGGRQHSA-N

物化性质

• 沸点：
  467.2±14.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 (4S,5R)-4-benzyl-5-hydroxymethyloxazolidin-2-one 在 三乙胺 作用下， 反应 2.0h， 以44%的产率得到(4-Benzyl-2-oxo-1,3-oxazolidin-5-yl)methyl methanesulfonate
  参考文献：
  名称：

  Synthesis and antimalarial activity of thioetherhydroxyethylsulfonamides, potential aspartyl protease inhibitors, Part 3

  摘要：

  A series of novel thioetherhydroxyethylsulfonamide derivatives has been synthesized from the coupling of intermediates 3-amino-4-phenyl-1-thioetherazine-butan-2-oles 6,7 with arenesulfonyl chlorides in good yields. Characterizations of products were achieved by NMR techniques and specifically for compound 8e by X-ray crystallography. Preliminary results of antimalarial activity in vitro against the Plasmodium falciparum W2 clone (chloroquine resistant and mefloquine sensitive) showed moderate activity for hydroxyethylsulfonamide 8f. In addition, none of the compounds tested showed cytotoxicity at high concentration tested against HepG2 and BGM cell lines. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.025
• 作为产物：
  描述：

  1-苄基-2,3-环氧正丙基-氨基甲酸叔丁酯 在 柠檬酸 作用下， 以 乙醇 、 正己烷 、 乙酸乙酯 为溶剂， 以80%的产率得到(4S,5R)-4-benzyl-5-hydroxymethyloxazolidin-2-one
  参考文献：
  名称：

  Method for producing epoxide crystal

  摘要：

  该发明涉及一种工业生产高纯度(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基环氧乙烷(晶体)或(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基醇的方法。生产N-碳酸酯保护的β-氨基环氧乙烷晶体的方法包括以下一项或多项步骤(a)至(d)：(a)将至少含有对映异构体作为杂质的(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基醇溶解于包括至少选择自芳香烃溶剂、饱和烃溶剂、水混合溶剂、丙酮和异丙醇的溶剂中，以去除不溶物质；(b)用碱处理(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基醇，从而将N-碳酸酯保护的β-氨基醇转化为(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基环氧乙烷；(c)用酸处理至少含有对映异构体作为杂质的(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基环氧乙烷，从而将对映异构体作为杂质转化为(4S, 5R)或(4R, 5S)噁唑烷-2-酮衍生物，并可在水或水混合溶剂中分离和去除所得的噁唑烷-2-酮衍生物；(d)在水和水亲和性有机溶剂的混合溶剂中结晶(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基环氧乙烷。通过本发明的方法，可以高效生产高纯度的(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基环氧乙烷或(2R, 3S)或(2S, 3R)-N-碳酸酯保护的β-氨基醇。

  公开号：

  US20020072621A1

文献信息

• Production method of beta-amino-alpha-hydroxycarboxylic acid
  申请人：AJINOMOTO CO. INC

  公开号：US20020151722A1

  公开（公告）日：2002-10-17

  The present invention provides a production method of an optically active &bgr;-amino-&agr;-hydroxycarboxylic acid, which includes the following steps (a)-(c): (a) treating an optically active N-carbamate protected &bgr;-amino epoxide with an acid to give an optically active 5-hydroxymethyl-2-oxazolidinone; (b) oxidizing the resulting compound in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy and hypochlorite to give an optically active 4-benzyl-2-oxo-5-oxazolidinecarboxylic acid; and (c) treating the 4-benzyl-2-oxo-5-oxazolidinecarboxylic acid with a base, and a production method of an optically active N-carbamate protected &bgr;-amino-&agr;-hydroxycarboxylic acid which includes protection of the amino group with a carbamate type protecting group. The industrial production method of the present invention can produce these compounds efficiently.

  本发明提供了一种光学活性β-氨基-α-羟基羧酸的生产方法，包括以下步骤(a)-(c)：(a) 用酸处理光学活性N-羰基保护的β-氨基环氧化合物，得到光学活性5-羟甲基-2-噁唑烷酮；(b) 在2,2,6,6-四甲基-1-哌啶氧和次氯酸盐存在下氧化所得化合物，得到光学活性4-苄基-2-氧代-5-噁唑烷羧酸；(c) 用碱处理4-苄基-2-氧代-5-噁唑烷羧酸，并且提供了一种光学活性N-羰基保护的β-氨基-α-羟基羧酸的生产方法，其中包括用羰酸酯型保护基保护氨基团。本发明的工业生产方法可以高效地生产这些化合物。
• A general stereocontrolled synthesis of hydroxyethylene dipeptide isosteres
  作者：Laurent Pégorier、Marc Larchevêque

  DOI：10.1016/0040-4039(95)00357-i

  日期：1995.4

  Hydroxyethylene dipeptide isosteres were synthesized by stereocontrolled hydroboration of homoallylic alcohols derived from syn protected aminoepoxides followed by chemoselective oxidation of the resulting primary alcohols.

  羟基亚乙基二肽电子等排体是由源自高烯丙基醇的立体控制合成硼氢化顺保护aminoepoxides然后将所得伯醇的化学选择性氧化。
• Production method of &bgr;-amino-&agr;-hydroxycarboxylic acid
  申请人：Ajinomoto Co., Inc.

  公开号：US06806384B2

  公开（公告）日：2004-10-19

  The present invention provides a production method of an optically active &bgr;-amino-&agr;-hydroxycarboxylic acid, which includes the following steps (a)-(c): (a) treating an optically active N-carbamate protected &bgr;-amino epoxide with an acid to give an optically active 5-hydroxymethyl-2-oxazolidinone; (b) oxidizing the resulting compound in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy and hypochlorite to give an optically active 4-benzyl-2-oxo-5-oxazolidinecarboxylic acid; and (c) treating the 4-benzyl-2-oxo-5-oxazolidinecarboxylic acid with a base, and a production method of an optically active N-carbamate protected &bgr;-amino-&agr;-hydroxycarboxylic acid which includes protection of the amino group with a carbamate type protecting group. The industrial production method of the present invention can produce these compounds efficiently.

  本发明提供了一种光学活性的β-氨基-α-羟基羧酸的生产方法，包括以下步骤(a)-(c)：(a)用酸处理光学活性的N-碳酸酯保护的β-氨基环氧化合物，以得到光学活性的5-羟甲基-2-噁唑烷酮；(b)在2,2,6,6-四甲基-1-哌啶氧自由基和次氯酸盐的存在下氧化所得化合物，以得到光学活性的4-苄基-2-氧代-5-噁唑烷羧酸；(c)用碱处理4-苄基-2-氧代-5-噁唑烷羧酸，以及一种包括用碳酸酯型保护基保护氨基的光学活性N-碳酸酯保护的β-氨基-α-羟基羧酸的生产方法。本发明的工业生产方法可以高效地生产这些化合物。
• Stereoselective synthesis of protected amino alkyl epoxides
  作者：Sergio Romeo、Daniel H. Rich

  DOI：10.1016/s0040-4039(00)73287-4

  日期：1994.7

  The mechanism of epoxidation of chiral allyl amines has been investigated. The intrinsic stereoselectivity for epoxidation is shown to be approximately 5:1 and is independent of the nitrogen substituent. However, the nature of the N-protecting group influences the stability of the undesired epoxide to the acidic media, with the minor diastereomer undergoing preferential decomposition. Conditions are reported for the highly stereoselective synthesis of epoxide 9R, an important building block in the synthesis of several enzyme inhibitors.
• US6806384B2
  申请人：——

  公开号：US6806384B2

  公开（公告）日：2004-10-19