[(2R,3S,4S,5R,6S)-2-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxymethyl]-4,5-dibenzoyloxy-6-phenylsulfanyloxan-3-yl] benzoate | 911816-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,4S,5R,6S)-2-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxymethyl]-4,5-dibenzoyloxy-6-phenylsulfanyloxan-3-yl] benzoate
• CAS: 911816-00-7
• 化学式: C₆₁H₆₆O₁₃SSi
• 分子量: 1067.34
• InChiKey: YOZIKXHKWMWELB-CXRBZREYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.55
• 重原子数：
  76
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  169
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5R,6S)-2-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxymethyl]-4,5-dibenzoyloxy-6-phenylsulfanyloxan-3-yl] benzoate 、 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of 1,2-cis galactosides: synthesis of a glycolipid containing Galα1-6Gal component from Zygomycetes species

  摘要：

  An alpha-selective galactosylation was demonstrated under various conditions. Among these alpha-galactoside approaches, high a-selectivity was achieved by the virtue of 4,6-O-di-tert-butylsitylene (DTBS) group. Yield was further improved by the influence of a 2-O-benzylated donor compared to 2-O-benzoylated donor. This method was then applied to the first highly stereoselective synthesis of a newly found trisaccharide glycosphingolipid in Zygomycetes species. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.181
• 作为产物：
  描述：

  phenyl 2,3-di-O-benzyl-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 [(2R,3S,4S,5R,6S)-2-[[(4aR,6S,7R,8R,8aS)-2,2-ditert-butyl-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl]oxymethyl]-4,5-dibenzoyloxy-6-phenylsulfanyloxan-3-yl] benzoate
  参考文献：
  名称：

  Stereoselective synthesis of 1,2-cis galactosides: synthesis of a glycolipid containing Galα1-6Gal component from Zygomycetes species

  摘要：

  An alpha-selective galactosylation was demonstrated under various conditions. Among these alpha-galactoside approaches, high a-selectivity was achieved by the virtue of 4,6-O-di-tert-butylsitylene (DTBS) group. Yield was further improved by the influence of a 2-O-benzylated donor compared to 2-O-benzoylated donor. This method was then applied to the first highly stereoselective synthesis of a newly found trisaccharide glycosphingolipid in Zygomycetes species. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.181