2-((2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-ethanol | 394212-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-ethanol
• CAS: 394212-00-1
• 化学式: C₇₁H₈₆O₁₂Si
• 分子量: 1159.54
• InChiKey: NLUUTDHOZZBSKH-BPKIJJHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.24
• 重原子数：
  84.0
• 可旋转键数：
  30.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  121.76
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-((2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-ethanol 在 咪唑 、 二硫化碳 、 sodium hydride 、 三正丁基氢锡 、 碘甲烷 、 偶氮二异丁腈 作用下， 以70%的产率得到tert-Butyl-dimethyl-{(2R,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-[2-((2R,3R,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-ethyl]-tetrahydro-pyran-2-ylmethoxy}-silane
  参考文献：
  名称：

  α(1-3)-Galactosyltransferase Inhibition Based on a New Type of Disubstrate Analogue This work was supported financially by the Deutschen Forschungsgemeinschaft and the Fonds der Chemischen Industrie.

  摘要：

  How do retaining glycosyltransferases function? To answer this question, UDP-Gal and galactose were covalently linked to form disubstrate analogues 1, of which surprisingly 1β and not 1α inhibited α(1-3)-galactosyltransferases very well. An understanding of this inhibition is a key to the pharmacological prevention of hyperacute rejection in pig to primate xenotransplantation.

  DOI：

  10.1002/1521-3773(20011105)40:21<4007::aid-anie4007>3.0.co;2-f
• 作为产物：
  描述：

  2,3,4,6-四-O-(苯基甲基)-D-半乳糖酸 D-内酯 在 四氧化锇 、 叔丁基锂 、 sodium methylate 、 对甲苯磺酸 、 臭氧 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 2-((2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yl)-1-[(2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-ethanol
  参考文献：
  名称：

  α(1-3)-Galactosyltransferase Inhibition Based on a New Type of Disubstrate Analogue This work was supported financially by the Deutschen Forschungsgemeinschaft and the Fonds der Chemischen Industrie.

  摘要：

  How do retaining glycosyltransferases function? To answer this question, UDP-Gal and galactose were covalently linked to form disubstrate analogues 1, of which surprisingly 1β and not 1α inhibited α(1-3)-galactosyltransferases very well. An understanding of this inhibition is a key to the pharmacological prevention of hyperacute rejection in pig to primate xenotransplantation.

  DOI：

  10.1002/1521-3773(20011105)40:21<4007::aid-anie4007>3.0.co;2-f