methyl 2,6-dideoxy-2-iodo-3-C-methyl-α-L-mannopyranoside | 1133161-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-dideoxy-2-iodo-3-C-methyl-α-L-mannopyranoside
• 英文别名: (2S,3S,4R,5R,6R)-5-iodo-6-methoxy-2,4-dimethyloxane-3,4-diol
• CAS: 1133161-84-8
• 化学式: C₈H₁₅IO₄
• 分子量: 302.109
• InChiKey: BFTGMGJXELKWIK-ZXVYDBTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,6-dideoxy-2-iodo-3-C-methyl-α-L-mannopyranoside 、 p-tolyl 2,3-anhydro-4-O-benzyl-1-thio-α-D-rhamnopyranoside 在 copper(II) bis(trifluoromethanesulfonate) 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 以112 mg的产率得到methyl 4-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->4)-2,6-dideoxy-3-C-methyl-α-L-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
• 作为产物：
  描述：

  甲醇 、 L-olivomycal 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到methyl 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