Acetic acid (2R,3R,4R,5R,6S,9S)-3-acetoxy-2-acetoxymethyl-5-azido-9-tert-butoxycarbonylamino-9-(3,4-dimethoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-10-en-4-yl ester | 502183-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Acetic acid (2R,3R,4R,5R,6S,9S)-3-acetoxy-2-acetoxymethyl-5-azido-9-tert-butoxycarbonylamino-9-(3,4-dimethoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-10-en-4-yl ester
• 英文别名: [(2R,3R,4R,5R,6S,9S)-3,4-diacetyloxy-5-azido-9-[(3,4-dimethoxyphenyl)methoxymethyl]-9-[(2-methylpropan-2-yl)oxycarbonylamino]-1,7-dioxaspiro[5.5]undec-10-en-2-yl]methyl acetate
• CAS: 502183-41-7
• 化学式: C₃₁H₄₂N₄O₁₃
• 分子量: 678.693
• InChiKey: JRWDQOPMYJENSE-RCHWXZQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  48
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  178
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R,6S,9S)-3-acetoxy-2-acetoxymethyl-5-azido-9-tert-butoxycarbonylamino-9-(3,4-dimethoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-10-en-4-yl ester 在 10percent Pd/C 氢气 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 (3R,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：

  [3-[(3R,4R,5S,6R)-3-Azido-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-tetrahydro-pyran-2-yl]-1-(3,4-dimethoxy-benzyloxymethyl)-1-hydroxymethyl-prop-2-ynyl]-carbamic acid tert-butyl ester 在 10percent Pd/C 4-二甲氨基吡啶 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 吡啶 、 正己烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 39.0h， 生成 Acetic acid (2R,3R,4R,5R,6S,9S)-3-acetoxy-2-acetoxymethyl-5-azido-9-tert-butoxycarbonylamino-9-(3,4-dimethoxy-benzyloxymethyl)-1,7-dioxa-spiro[5.5]undec-10-en-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