benzyl 3-O-(tert-butyldimethylsilyl)-4-O-isobutyryl-2,6-dideoxy-2-iodo-3-C-methyl-α-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 | 1133162-93-2

• 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-2-iodo-3-C-methyl-α-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
• 英文别名: [(2R,3R,4R,6R)-4-[(2S,4R,5R,6R)-5-benzoyloxy-4-[(2S,3R,4R,5S,6S)-4-[tert-butyl(dimethyl)silyl]oxy-3-iodo-4,6-dimethyl-5-(2-methylpropanoyloxy)oxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-methyl-6-phenylmethoxyoxan-3-yl] benzoate
• CAS: 1133162-93-2
• 化学式: C₅₀H₆₇IO₁₃Si
• 分子量: 1031.06
• InChiKey: CZCAPLQAIOOANT-FDLANTRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.59
• 重原子数：
  65
• 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

• 作为产物：
  描述：

  1,5-anhydro-3-O-(tert-butyldimethylsilyl)-4-O-isobutyryl-1,2,6-trideoxy-3-C-methyl-L-arabino-hex-1-enitol 、 benzyl 4-O-benzoyl-3-O-(4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,6-dideoxy-β-D-arabino-hexopyranoside 4,4'-dibenzoate 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 benzyl 3-O-(tert-butyldimethylsilyl)-4-O-isobutyryl-2,6-dideoxy-2-iodo-3-C-methyl-α-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 、 benzyl 3-O-(tert-butyldimethylsilyl)-4-O-isobutyryl-2,6-dideoxy-2-iodo-3-C-methyl-β-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
  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