Acetic acid (2R,3R,4R,5R,6S,9R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-9-tert-butoxycarbonylamino-9-hydroxymethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester | 502183-48-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4R,5R,6S,9R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-9-tert-butoxycarbonylamino-9-hydroxymethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester
• 英文别名: [(2R,3R,4R,5R,6S,9R)-5-acetamido-3,4-diacetyloxy-9-(hydroxymethyl)-9-[(2-methylpropan-2-yl)oxycarbonylamino]-1,7-dioxaspiro[5.5]undecan-2-yl]methyl acetate
• CAS: 502183-48-4
• 化学式: C₂₄H₃₈N₂O₁₂
• 分子量: 546.572
• InChiKey: DNFTVHKLOQQLFE-OQIHLKNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  185
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R,6S,9R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-9-tert-butoxycarbonylamino-9-hydroxymethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester 在 碳酸氢钠 、 戴斯-马丁氧化剂 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 21.0h， 以90%的产率得到(3S,6S,8R,9R,10R,11R)-9,10-Diacetoxy-8-acetoxymethyl-11-acetylamino-3-tert-butoxycarbonylamino-1,7-dioxa-spiro[5.5]undecane-3-carboxylic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Conformationally Constrained Glycosylated Amino Acids Using an Enzyme-Catalyzed Desymmetrization

  摘要：

  As part of an effort to probe the mechanism by which glycosyltransferases recognize glycoproteins and assemble the core structures of O-linked oligosaccharides, constrained glycopeptides, compounds 2 and 3, based on the alpha-N-acetylgalactosaminyl serine substructure 1, were designed. In this paper we describe a stereoselective preparation of protected versions of these compounds. A pig liver esterase-catalyzed enzymatic desymmetrization of a diacetate substrate, 10, was employed as a key component in the synthesis.

  DOI：

  10.1021/jo020532t
• 作为产物：
  描述：

  [(3R,8R,9R,10R,11R)-11-Azido-3-(3,4-dimethoxy-benzyloxymethyl)-9,10-dihydroxy-8-hydroxymethyl-1,7-dioxa-spiro[5.5]undec-4-en-3-yl]-carbamic acid tert-butyl ester 在 10percent Pd/C 4-二甲氨基吡啶 、 氢气 作用下， 以 吡啶 、 乙酸乙酯 为溶剂， 反应 29.0h， 生成 Acetic acid (2R,3R,4R,5R,6S,9R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-9-tert-butoxycarbonylamino-9-hydroxymethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Conformationally Constrained Glycosylated Amino Acids Using an Enzyme-Catalyzed Desymmetrization

  摘要：

  As part of an effort to probe the mechanism by which glycosyltransferases recognize glycoproteins and assemble the core structures of O-linked oligosaccharides, constrained glycopeptides, compounds 2 and 3, based on the alpha-N-acetylgalactosaminyl serine substructure 1, were designed. In this paper we describe a stereoselective preparation of protected versions of these compounds. A pig liver esterase-catalyzed enzymatic desymmetrization of a diacetate substrate, 10, was employed as a key component in the synthesis.

  DOI：

  10.1021/jo020532t