tert-butyl 2-(((4R,5S)-5-hydroxy-2,2-dimethyl-3-(2-phenoxyacetyl)thiazolidine-4-carboxamido)oxy)acetate | 1334521-68-4

• 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: tert-butyl 2-(((4R,5S)-5-hydroxy-2,2-dimethyl-3-(2-phenoxyacetyl)thiazolidine-4-carboxamido)oxy)acetate
• 英文别名: tert-butyl 2-[[(4R,5S)-5-hydroxy-2,2-dimethyl-3-(2-phenoxyacetyl)-1,3-thiazolidine-4-carbonyl]amino]oxyacetate
• CAS: 1334521-68-4
• 化学式: C₂₀H₂₈N₂O₇S
• 分子量: 440.518
• InChiKey: LEJWMBNDAVEYIT-AEFFLSMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(((4R,5S)-5-hydroxy-2,2-dimethyl-3-(2-phenoxyacetyl)thiazolidine-4-carboxamido)oxy)acetate 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以46%的产率得到tert-butyl 2-(((1R,5R)-3,3-dimethyl-7-oxo-2-(2-phenoxyacetyl)-4-thia-2,6-diazabicyclo[3.2.0]heptan-6-yl)oxy)acetate
  参考文献：
  名称：

  Asymmetric synthesis of monocyclic β-lactams from l-cysteine using photochemistry

  摘要：

  An asymmetric method to synthesize cis-configured beta-lactams using photochemistry has been developed. Aerobic photo-oxidation of L-cysteine-derived thiazolidine hydroxamate esters afforded C-3 hydroxylated products which when cyclized and deprotected gave the corresponding N-protio monocyclic beta-lactams. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2011.07.085
• 作为产物：
  描述：

  2-(氨基氧基)乙酸叔丁酯 在 二甲基硫 、 氧气 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl 2-(((4R,5S)-5-hydroxy-2,2-dimethyl-3-(2-phenoxyacetyl)thiazolidine-4-carboxamido)oxy)acetate
  参考文献：
  名称：

  Asymmetric synthesis of monocyclic β-lactams from l-cysteine using photochemistry

  摘要：

  An asymmetric method to synthesize cis-configured beta-lactams using photochemistry has been developed. Aerobic photo-oxidation of L-cysteine-derived thiazolidine hydroxamate esters afforded C-3 hydroxylated products which when cyclized and deprotected gave the corresponding N-protio monocyclic beta-lactams. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2011.07.085

文献信息

• Asymmetric synthesis of monocyclic β-lactams from l-cysteine using photochemistry
  作者：Xiao Lu、Timothy E. Long

  DOI：10.1016/j.tetlet.2011.07.085

  日期：2011.9

  An asymmetric method to synthesize cis-configured beta-lactams using photochemistry has been developed. Aerobic photo-oxidation of L-cysteine-derived thiazolidine hydroxamate esters afforded C-3 hydroxylated products which when cyclized and deprotected gave the corresponding N-protio monocyclic beta-lactams. Published by Elsevier Ltd.