(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-N,N-dimethyl-2-methylsulfanyl-propionamide | 819069-95-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-N,N-dimethyl-2-methylsulfanyl-propionamide
• 英文别名: (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-N,N-dimethyl-2-methylsulfanylpropanamide
• CAS: 819069-95-9
• 化学式: C₁₇H₃₅NO₄SSi
• 分子量: 377.621
• InChiKey: YFSGMCFWXHOWIK-MCIONIFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  73.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-N,N-dimethyl-2-methylsulfanyl-propionamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到(2S,3R)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-N,N-dimethyl-2-methylsulfanyl-propionamide
  参考文献：
  名称：

  Isomerization of E-α,β-epoxyamides to Z-α,β-epoxyamides and synthetic applications based on regio- and stereoselective oxirane ring openings

  摘要：

  The regioselective opening reaction of 2,3-epoxyanudes with Various nucleophiles offers a variety of beta-hydroxyamides with diverse synthetic utility depending on the introduced nucleophile. Due to the exclusive stereoselectivity in the formation of trans epoxyamides in reactions of aldehydes with stabilized sulfur ylides, We studied the isomerization of trans epoxyamides into the cis isomers with the objective of obtaining the corresponding syn opening products, which together with the anti isomers represent a variety of enantiomerically Pure building blocks. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.034
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-N,N-dimethyl-2-methylsulfanyl-propionamide
  参考文献：
  名称：

  Isomerization of E-α,β-epoxyamides to Z-α,β-epoxyamides and synthetic applications based on regio- and stereoselective oxirane ring openings

  摘要：

  The regioselective opening reaction of 2,3-epoxyanudes with Various nucleophiles offers a variety of beta-hydroxyamides with diverse synthetic utility depending on the introduced nucleophile. Due to the exclusive stereoselectivity in the formation of trans epoxyamides in reactions of aldehydes with stabilized sulfur ylides, We studied the isomerization of trans epoxyamides into the cis isomers with the objective of obtaining the corresponding syn opening products, which together with the anti isomers represent a variety of enantiomerically Pure building blocks. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.034