benzyl 4-O-acetyl-3-O-t-butyldimethylsilyl-2,6-dideoxy-2-iodo-3-C-methyl-α-L-mannopyranoside | 1133161-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4-O-acetyl-3-O-t-butyldimethylsilyl-2,6-dideoxy-2-iodo-3-C-methyl-α-L-mannopyranoside
• 英文别名: [(2S,3S,4R,5R,6R)-4-[tert-butyl(dimethyl)silyl]oxy-5-iodo-2,4-dimethyl-6-phenylmethoxyoxan-3-yl] acetate
• CAS: 1133161-56-4
• 化学式: C₂₂H₃₅IO₅Si
• 分子量: 534.507
• InChiKey: NQFCUFTYANRWIV-RKLWYLGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.46
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl 4-O-acetyl-3-O-t-butyldimethylsilyl-2,6-dideoxy-2-iodo-3-C-methyl-α-L-mannopyranoside 在 二异丁基氢化铝 、 甲醇 、 rochelle salt 作用下， 以 二氯甲烷 、 正戊烷 为溶剂， 反应 5.08h， 以77%的产率得到(2S,3S,4R,5R,6R)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-iodo-2,4-dimethyltetrahydro-2H-pyran-3-ol
  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：

  4-O-acetyl-1,5-anhydro-3-O-t-butyldimethylsilyl-1,2,6-trideoxy-3-C-methyl-L-arabino-hex-1-enitol 、 苯甲醇 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 以59%的产率得到benzyl 4-O-acetyl-3-O-t-butyldimethylsilyl-2,6-dideoxy-2-iodo-3-C-methyl-α-L-mannopyranoside
  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