benzyl 3-O-(tert-butyldimethylsilyl)-4-O-isobutyryl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside | 1133163-00-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3-O-(tert-butyldimethylsilyl)-4-O-isobutyryl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside
• 英文别名: [(2R,3R,4R,6R)-4-[(2S,4R,5R,6R)-5-benzoyloxy-4-[(2S,4S,5S,6S)-4-[tert-butyl(dimethyl)silyl]oxy-4,6-dimethyl-5-(2-methylpropanoyloxy)oxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-methyl-6-phenylmethoxyoxan-3-yl] benzoate
• CAS: 1133163-00-4
• 化学式: C₅₀H₆₈O₁₃Si
• 分子量: 905.168
• InChiKey: TWXYUYQURVIYBM-MZBSYGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.18
• 重原子数：
  64
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-(tert-butyldimethylsilyl)-4-O-isobutyryl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside 在 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to 2,6-Dideoxypyranosides

  摘要：

  We describe here the first use of 2,3-anhydrosugars as glycosylating agents for the preparation of 2-deoxypyranosides. In particular, the methodology was used to assemble 2,6-dideoxysugar glycosides. Glycosylation of a panel of alcohols with one of two 6-deoxy-2,3-anhydrosugar thioglycosides (8 and 9) in the presence of a Lewis acid afforded 2,6-dideoxy-2-thiotolyl glycoside products in generally excellent yields with an exclusively syn relationship between the aglycon and the C-3 hydroxyl group. Removal of the 2-thiotolyl group can be achieved upon reaction with tri-n-butyltin hydride and AIBN to give the corresponding 2,6-dideoxy pyranosides. Once developed, the method was applied to the synthesis of oligosaccharide moieties in the natural products apoptolidin and olivomycin A.

  DOI：

  10.1021/jo900131a
• 作为产物：
  描述：

  benzyl 3-O-(tert-butyldimethylsilyl)-4-O-isobutyryl-2,6-dideoxy-2-iodo-3-C-methyl-L-mannopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以95%的产率得到benzyl 3-O-(tert-butyldimethylsilyl)-4-O-isobutyryl-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to 2,6-Dideoxypyranosides

  摘要：

  We describe here the first use of 2,3-anhydrosugars as glycosylating agents for the preparation of 2-deoxypyranosides. In particular, the methodology was used to assemble 2,6-dideoxysugar glycosides. Glycosylation of a panel of alcohols with one of two 6-deoxy-2,3-anhydrosugar thioglycosides (8 and 9) in the presence of a Lewis acid afforded 2,6-dideoxy-2-thiotolyl glycoside products in generally excellent yields with an exclusively syn relationship between the aglycon and the C-3 hydroxyl group. Removal of the 2-thiotolyl group can be achieved upon reaction with tri-n-butyltin hydride and AIBN to give the corresponding 2,6-dideoxy pyranosides. Once developed, the method was applied to the synthesis of oligosaccharide moieties in the natural products apoptolidin and olivomycin A.

  DOI：

  10.1021/jo900131a