(R)-[1-(tert-butyldimethylsilanyloxymethyl)-1-(3,4-dimethoxybenzyloxymethyl)prop-2-ynyl]carbamic acid tert-butyl ester | 502183-39-3

• 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: (R)-[1-(tert-butyldimethylsilanyloxymethyl)-1-(3,4-dimethoxybenzyloxymethyl)prop-2-ynyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2R)-1-[tert-butyl(dimethyl)silyl]oxy-2-[(3,4-dimethoxyphenyl)methoxymethyl]but-3-yn-2-yl]carbamate
• CAS: 502183-39-3
• 化学式: C₂₅H₄₁NO₆Si
• 分子量: 479.689
• InChiKey: KXEVXRWTPGGUTQ-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-[1-(tert-butyldimethylsilanyloxymethyl)-1-(3,4-dimethoxybenzyloxymethyl)prop-2-ynyl]carbamic acid tert-butyl ester 、 2-azido-3,4,6-tri-O-(tert-butyldimethylsilyl)-2-deoxy-D-galactono-1,5-lactone 在 六甲基磷酰三胺 、 正丁基锂 、 盐酸 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 甲醇 为溶剂， 反应 3.92h， 生成 、
  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：

  3,4-二甲氧基苄醇 在 氢氧化钾 、 camphor-10-sulfonic acid 、 三(3,6-二氧杂庚基)胺 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (R)-[1-(tert-butyldimethylsilanyloxymethyl)-1-(3,4-dimethoxybenzyloxymethyl)prop-2-ynyl]carbamic acid tert-butyl 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