(2R,3S,4R)-1-O-(tert-butyl(diphenyl)silyl)-3,4-O-isopropylidene-15-methyl-5-hexadecene-1,2,3,4-tetrol | 911371-54-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-1-O-(tert-butyl(diphenyl)silyl)-3,4-O-isopropylidene-15-methyl-5-hexadecene-1,2,3,4-tetrol
• 英文别名: (1R)-2-[tert-butyl(diphenyl)silyl]oxy-1-[(4S,5R)-2,2-dimethyl-5-[(E)-11-methyldodec-1-enyl]-1,3-dioxolan-4-yl]ethanol
• CAS: 911371-54-5
• 化学式: C₃₆H₅₆O₄Si
• 分子量: 580.924
• InChiKey: GHFXHULMEUUFQY-PIPPQBPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.78
• 重原子数：
  41
• 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：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-1-O-(tert-butyl(diphenyl)silyl)-3,4-O-isopropylidene-15-methyl-5-hexadecene-1,2,3,4-tetrol 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 以95%的产率得到(2R,3S,4R)-1-O-(tert-butyl(diphenyl)silyl)-3,4-O-isopropylidene-15-methylhexadecane-1,2,3,4-tetrol
  参考文献：
  名称：

  Total Synthesis of Agelagalastatin

  摘要：

  The total synthesis of agelagalastatin, an antineoplastic glycosphingolipid, has been achieved. The synthesis involved an alpha-selective glycosylation of the ceramide moiety with the trisaccharide fluoride. The trisaccharide component was constructed employing the CB glycoside method which permitted a completely alpha-stereoselective galactofuranosylation.

  DOI：

  10.1021/ol061444o
• 作为产物：
  描述：

  (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol 在 正丁基锂 、 generation II Grubbs catalyst 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.5h， 生成 (2R,3S,4R)-1-O-(tert-butyl(diphenyl)silyl)-3,4-O-isopropylidene-15-methyl-5-hexadecene-1,2,3,4-tetrol
  参考文献：
  名称：

  Total Synthesis of Agelagalastatin

  摘要：

  The total synthesis of agelagalastatin, an antineoplastic glycosphingolipid, has been achieved. The synthesis involved an alpha-selective glycosylation of the ceramide moiety with the trisaccharide fluoride. The trisaccharide component was constructed employing the CB glycoside method which permitted a completely alpha-stereoselective galactofuranosylation.

  DOI：

  10.1021/ol061444o

文献信息

• Total Synthesis of Agelagalastatin
  作者：Yong Joo Lee、Bo-Young Lee、Heung Bae Jeon、Kwan Soo Kim

  DOI：10.1021/ol061444o

  日期：2006.8.1

  The total synthesis of agelagalastatin, an antineoplastic glycosphingolipid, has been achieved. The synthesis involved an alpha-selective glycosylation of the ceramide moiety with the trisaccharide fluoride. The trisaccharide component was constructed employing the CB glycoside method which permitted a completely alpha-stereoselective galactofuranosylation.