(3S,4R)-3-(acetylamino)-4-methyl-2-oxetanone | 83151-09-1

• 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: (3S,4R)-3-(acetylamino)-4-methyl-2-oxetanone
• 英文别名: N-Acetyl-L-threonine β-lactone；SQ 26,517；(2R-cis)-N-(2-Methyl-4-oxo-3-oxetanyl)actamide；N-[(2R,3S)-2-methyl-4-oxooxetan-3-yl]acetamide
• CAS: 83151-09-1
• 化学式: C₆H₉NO₃
• 分子量: 143.142
• InChiKey: ZCSKPKMAWTYOSK-WUJLRWPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3S,4R)-3-氨基-4-甲基氧-2-酮 、 乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到(3S,4R)-3-(acetylamino)-4-methyl-2-oxetanone
  参考文献：
  名称：

  Synthesis and acylation of salts of L-threonine .beta.-lactone: a route to .beta.-lactone antibiotics

  摘要：

  The synthesis and N-acylation of beta-lactones derived from L-threonine and L-allo-threonine were investigated. Treatment of N-[(o-nitrophenyl)sulfenyl]-L-threonine (7a) and N-[(o-nitrophenyl)sulfenyl]-L-allo-threonine (7b) with 4-bromobenzenesulfonyl chloride in pyridine at -43 to -0-degrees-C gives the corresponding-beta-lactones 8a and 8b, respectively, in 45-56% yields. These can be deprotected with thiophenol or p-thiocresol in the presence of p-toluenesulfonic acid to produce optically pure salts of L-threonine-beta-lactone (9a) and its allo isomer 9b (65-92%). Compound 9a is readily acylated by reagents such as acid chlorides (e.g., acetyl, benzoyl) and mixed anhydrides to afford N-acyl-beta-substituted-beta-lactones such as 10 (antibiotic SQ 26,517), 14, 15, and 16 in good yield (84-92%). Reaction of beta-lactones 8a, 8b, and 9a with HBr in acetic acid results in nucleophilic ring opening by bromide at the beta-position to give pure isomers of 2-amino-3-bromobutanoic acid.

  DOI：

  10.1021/jo00003a062

文献信息

• A novel transacylation method for the synthesis of α-N-acyl-β-lactones; application to (±)-diacetylobafluorin and (+)-SQ 26,517
  作者：M. Narayana Rao、Anil G. Holkar、Nagaraj R. Ayyangar

  DOI：10.1039/c39910001007

  日期：——

  Stereoselective synthesis of (±)-diacetylobafluorin and (+)-SQ 26,517 has been accomplished via transacylation of α-N-(2-nitrophenyl)sulphenyl-β-lactones with 2-acylmercaptobenzothiazoles.

  通过与2-酰基巯基苯噻唑的转酰基化反应，实现了(±)-二乙酰巴氟林和(+)SQ 26,517的立体选择性合成。
• Lactone-based probes and methods of use thereof
  申请人：REGENTS OF THE UNIVERSITY OF MINNESOTA

  公开号：US10822318B2

  公开（公告）日：2020-11-03

  The invention provides a compound of formula I: or a salt thereof, wherein R1, R2, R3, R4, L1, L2 and Y have any of the values described in the specification, as well as compositions comprising a compound of formula I. The compounds are useful for labeling penicillin-binding proteins (PBPs).

  本发明提供了一种式 I 的化合物： 或其盐，其中 R1、R2、R3、R4、L1、L2 和 Y 具有说明书中描述的任一数值，以及包含式 I 化合物的组合物。这些化合物可用于标记青霉素结合蛋白（PBPs）。
• PU, YUNLONG;MARTIN, FIONNA M.;VEDERAS, JOHN C., J. ORG. CHEM., 56,(1991) N, C. 1280-1283
  作者：PU, YUNLONG、MARTIN, FIONNA M.、VEDERAS, JOHN C.

  DOI：——

  日期：——
• Synthesis and acylation of salts of L-threonine .beta.-lactone: a route to .beta.-lactone antibiotics
  作者：Yunlong Pu、Fionna M. Martin、John C. Vederas

  DOI：10.1021/jo00003a062

  日期：1991.2

  The synthesis and N-acylation of beta-lactones derived from L-threonine and L-allo-threonine were investigated. Treatment of N-[(o-nitrophenyl)sulfenyl]-L-threonine (7a) and N-[(o-nitrophenyl)sulfenyl]-L-allo-threonine (7b) with 4-bromobenzenesulfonyl chloride in pyridine at -43 to -0-degrees-C gives the corresponding-beta-lactones 8a and 8b, respectively, in 45-56% yields. These can be deprotected with thiophenol or p-thiocresol in the presence of p-toluenesulfonic acid to produce optically pure salts of L-threonine-beta-lactone (9a) and its allo isomer 9b (65-92%). Compound 9a is readily acylated by reagents such as acid chlorides (e.g., acetyl, benzoyl) and mixed anhydrides to afford N-acyl-beta-substituted-beta-lactones such as 10 (antibiotic SQ 26,517), 14, 15, and 16 in good yield (84-92%). Reaction of beta-lactones 8a, 8b, and 9a with HBr in acetic acid results in nucleophilic ring opening by bromide at the beta-position to give pure isomers of 2-amino-3-bromobutanoic acid.