methyl 4-<1-(methoxymethyl)-2-oxo-4-azetidinyl>-β-hydroxybutyrate | 133374-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: methyl 4-<1-(methoxymethyl)-2-oxo-4-azetidinyl>-β-hydroxybutyrate
• 英文别名: methyl 4-(1-methoxymethoxy-2-oxo-4-azetidinyl)-β-hydroxybutyrate；Methyl 3-hydroxy-4-[1-(methoxymethoxy)-4-oxoazetidin-2-yl]butanoate
• CAS: 133374-72-8
• 化学式: C₁₀H₁₇NO₆
• 分子量: 247.248
• InChiKey: GZDJHAHUQIUNMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-<1-(methoxymethyl)-2-oxo-4-azetidinyl>-β-hydroxybutyrate 在 dirhodium tetraacetate 吡啶 、 chromium(VI) oxide 、 4-羧基苯磺叠氮 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 methyl 2-oxo-1-carba-1-dethiapenam-3-carboxylate
  参考文献：
  名称：

  Direct conversion of N-alkoxy .beta.-lactams to carbapenams: application to the synthesis of the bicyclic PS-5 keto ester

  摘要：

  The synthesis and direct conversion of N-alkoxy beta-lactams to the carbapenam ring system is described. This novel cyclization apparently proceeds by initial carbene-mediated ylide formation with concomitant rearrangement. The title reaction is applied to the construction of the methyl ester of the bicyclic beta-lactam precursor of PS-5.

  DOI：

  10.1021/jo00008a022
• 作为产物：
  描述：

  methyl 4-<1-(benzyloxy)-2-oxo-4-azetidinyl>-β-<(tert-butyldimethylsilyl)oxy>butyrate 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 溶剂黄146 、 乙酸乙酯 、 乙腈 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 19.25h， 生成 methyl 4-<1-(methoxymethyl)-2-oxo-4-azetidinyl>-β-hydroxybutyrate
  参考文献：
  名称：

  Direct conversion of N-alkoxy .beta.-lactams to carbapenams: application to the synthesis of the bicyclic PS-5 keto ester

  摘要：

  The synthesis and direct conversion of N-alkoxy beta-lactams to the carbapenam ring system is described. This novel cyclization apparently proceeds by initial carbene-mediated ylide formation with concomitant rearrangement. The title reaction is applied to the construction of the methyl ester of the bicyclic beta-lactam precursor of PS-5.

  DOI：

  10.1021/jo00008a022

文献信息

• Process for bicyclic beta-lactams
  申请人：THE UNIVERSITY OF NOTRE DAME DU LAC

  公开号：EP0460881A1

  公开（公告）日：1991-12-11

  1-Carbapenam-2-one-3-carboxylic acid and 1-carba-3-hydroxy-3-cephem-4-carboxylic acid and esters thereof are provided by a process comprising a rhodium C₂-C₁₀ carboxylate catalyzed cyclization of an ester of a 4-(1-alkoxy- or 1-substituted alkoxy)-2-oxo-4-azetidinyl)-α-diazo-β-ketobutyric acid and an ester of a 5-(1-alkoxy- or 1-substituted alkoxy-2-oxo-4-azetidinyl)-α-diazo-β-ketovaleric acid respectively. The process is carried out in an inert organic solvent at a temperature between about 15° C and about 85° C. The 1-carba bicyclic β-lactams are intermediates for preparing antibiotics.

  1-碳青霉酰胺-2-酮-3-羧酸和 1-碳巴-3-羟基-3-头孢-4-羧酸及其酯是通过一种工艺提供的，该工艺包括 C₂-C₁₀羧酸铑催化环化 4-(1-烷氧基-或 1-取代烷氧基)-2-氧代-4-氮杂环丁基)-α-偶氮-β-酮丁酸的酯和 5-(1-烷氧基-或 1-取代烷氧基-2-氧代-4-氮杂环丁基)-α-偶氮-β-酮戊酸的酯的环化。该工艺在惰性有机溶剂中进行，温度介于约 15° C 和约 85° C 之间。1-羧基双环 β-内酰胺是制备抗生素的中间体。
• SLOUKA, JAN, COLLECT. CHECHOSL. CHEM. COMMUN., 55,(1990) N2, C. 2967-2976
  作者：SLOUKA, JAN

  DOI：——

  日期：——
• US5051502A
  申请人：——

  公开号：US5051502A

  公开（公告）日：1991-09-24
• US5106968A
  申请人：——

  公开号：US5106968A

  公开（公告）日：1992-04-21
• Direct conversion of N-alkoxy .beta.-lactams to carbapenams: application to the synthesis of the bicyclic PS-5 keto ester
  作者：Matthew A. Williams、Chi Nung Hsiao、Marvin J. Miller

  DOI：10.1021/jo00008a022

  日期：1991.4

  The synthesis and direct conversion of N-alkoxy beta-lactams to the carbapenam ring system is described. This novel cyclization apparently proceeds by initial carbene-mediated ylide formation with concomitant rearrangement. The title reaction is applied to the construction of the methyl ester of the bicyclic beta-lactam precursor of PS-5.