ethyl 6-O-tert-butyldiphenylsilyl-4-O-methoxycarbonyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside | 162934-22-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ethyl 6-O-tert-butyldiphenylsilyl-4-O-methoxycarbonyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
• 英文别名: [(2R,3R,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-ethoxy-3,6-dihydro-2H-pyran-3-yl] methyl carbonate
• CAS: 162934-22-7
• 化学式: C₂₆H₃₄O₆Si
• 分子量: 470.638
• InChiKey: GOGUOBRZGWJRNZ-SMIHKQSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.03
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-tert-butyldiphenylsilyl-4-O-methoxycarbonyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 、 双丙酮葡萄糖 在 tris-(dibenzylideneacetone)dipalladium(0) 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以76%的产率得到
  参考文献：
  名称：

  Stereoselective Palladium(0)-Mediated Synthesis of Unsaturated 1,4-Disaccharides

  摘要：

  Unsaturated 1,4-disaccharides are obtained in quite good yields by alkylation of ethyl alpha-O-Delta(2)-glycosides, having a leaving group at C-4, with various 1-hydroxycarbohydrates in the presence of a catalytic amount of palladium(0). The reaction is regio- and stereospecific for alpha-erythro enosides 3 and 5, and only stereospecific in the case of the beta-threo enoside 7, alkylation occurring at C-4 and C-2 in this case.

  DOI：

  10.1080/07328309708006546
• 作为产物：
  描述：

  (2R,3S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethoxy-3,6-dihydro-2H-pyran-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 60.0h， 生成 ethyl 6-O-tert-butyldiphenylsilyl-4-O-methoxycarbonyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
  参考文献：
  名称：

  Stereoselective Palladium(0)-Mediated Synthesis of Unsaturated 1,4-Disaccharides

  摘要：

  Unsaturated 1,4-disaccharides are obtained in quite good yields by alkylation of ethyl alpha-O-Delta(2)-glycosides, having a leaving group at C-4, with various 1-hydroxycarbohydrates in the presence of a catalytic amount of palladium(0). The reaction is regio- and stereospecific for alpha-erythro enosides 3 and 5, and only stereospecific in the case of the beta-threo enoside 7, alkylation occurring at C-4 and C-2 in this case.

  DOI：

  10.1080/07328309708006546

文献信息

• Efficient Palladium(0)-Catalyzed Synthesis of Alkenyl 1-Thioglycosides and Thiodisaccharides
  作者：Anna Zawisza、Boguslaw Kryczka、Paul Lhoste、Stanislaw Porwanski、Denis Sinou

  DOI：10.1080/07328300008544118

  日期：2000.1

  Unsaturated thiodisaccharides are obtained in good yields by alkylation of ethyl alpha-Q-Delta(2)-glycosides, having a leaving group at C-4, with various thiocarbohydrates in the presence of a catalytic amount of palladium(0). The reaction is regio- and stereospecific for the alpha-erythro enoside, and only stereospecific in the case of the alpha-threo enoside, alkylation occurring at C-4 and C-2. In all cases, only the beta-anomer is formed.
• Stereoselective palladium(0)-mediated synthesis of 1,4-disaccharides
  作者：Denis Sinou、Isabelle Frappa、Paul Lhoste、Stanislaw Porwanski、Boguslaw Kryczka

  DOI：10.1016/0040-4039(94)02480-y

  日期：1995.2

  Unsaturated 1,4-disaccharides are obtained in fairly good yields by alkylation of ethyl alpha-O-Delta(2)-glycosides which have a leaving group at the position 4 with various carbohg drates havillg a free anomeric hydroxyl group in the presence of a catalytic amount of palladium(0).
• Stereoselective Palladium(0)-Mediated Synthesis of Unsaturated 1,4-Disaccharides
  作者：Isabelle Frappa、Boguslaw Kryczka、Paul Lhoste、Stanislaw Porwanski、Denis Sinou

  DOI：10.1080/07328309708006546

  日期：1997.8.1

  Unsaturated 1,4-disaccharides are obtained in quite good yields by alkylation of ethyl alpha-O-Delta(2)-glycosides, having a leaving group at C-4, with various 1-hydroxycarbohydrates in the presence of a catalytic amount of palladium(0). The reaction is regio- and stereospecific for alpha-erythro enosides 3 and 5, and only stereospecific in the case of the beta-threo enoside 7, alkylation occurring at C-4 and C-2 in this case.