Acetamido 2,2,5-trimethyl-1,3-dioxane-5-carboxylate | 1255518-22-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetamido 2,2,5-trimethyl-1,3-dioxane-5-carboxylate
• 英文别名: acetamido 2,2,5-trimethyl-1,3-dioxane-5-carboxylate
• CAS: 1255518-22-9
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: NAVGAGVKMGSWHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  39-O-desmethoxy-rapamycin 、 Acetamido 2,2,5-trimethyl-1,3-dioxane-5-carboxylate 在 Lipase PS (Amano) 作用下， 以 甲基叔丁基醚 为溶剂， 反应 60.0h， 以75%的产率得到
  参考文献：
  名称：

  Regioselective lipase-catalyzed acylation of 41-desmethoxy-rapamycin without vinyl esters

  摘要：

  Selective lipase-catalyzed acylation of 41-desmethoxyrapamycin has been achieved with a quaternary carboxylic acid avoiding the use of vinyl ester activation. Among the acyl donors investigated, the novel butanedione-monooxime and the N-acetylhydroxamate ester proved to be the most efficient donors, comparable in reactivity to the undesired vinyl ester and allowing selective, preparative acylation on gram scale in excellent yields. These new donors are proposed as sustainable and process-friendly alternatives to the widely used vinyl ester substrate activation in lipase-catalyzed acylations of secondary alcohols. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.020
• 作为产物：
  描述：

  2,2,5-三甲基-1,3-二恶烷-5-甲酸 、 乙酰氧肟酸 在 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 、 正己烷 、 乙酸乙酯 为溶剂， 反应 5.0h， 以560 mg的产率得到Acetamido 2,2,5-trimethyl-1,3-dioxane-5-carboxylate
  参考文献：
  名称：

  Regioselective lipase-catalyzed acylation of 41-desmethoxy-rapamycin without vinyl esters

  摘要：

  Selective lipase-catalyzed acylation of 41-desmethoxyrapamycin has been achieved with a quaternary carboxylic acid avoiding the use of vinyl ester activation. Among the acyl donors investigated, the novel butanedione-monooxime and the N-acetylhydroxamate ester proved to be the most efficient donors, comparable in reactivity to the undesired vinyl ester and allowing selective, preparative acylation on gram scale in excellent yields. These new donors are proposed as sustainable and process-friendly alternatives to the widely used vinyl ester substrate activation in lipase-catalyzed acylations of secondary alcohols. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.020

文献信息

• Regioselective lipase-catalyzed acylation of 41-desmethoxy-rapamycin without vinyl esters
  作者：Thomas Storz、Jianxin Gu、Bogdan Wilk、Eric Olsen

  DOI：10.1016/j.tetlet.2010.08.020

  日期：2010.10

  Selective lipase-catalyzed acylation of 41-desmethoxyrapamycin has been achieved with a quaternary carboxylic acid avoiding the use of vinyl ester activation. Among the acyl donors investigated, the novel butanedione-monooxime and the N-acetylhydroxamate ester proved to be the most efficient donors, comparable in reactivity to the undesired vinyl ester and allowing selective, preparative acylation on gram scale in excellent yields. These new donors are proposed as sustainable and process-friendly alternatives to the widely used vinyl ester substrate activation in lipase-catalyzed acylations of secondary alcohols. (C) 2010 Elsevier Ltd. All rights reserved.