methyl 4-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->4)-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranoside | 1133161-97-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->4)-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranoside
• 英文别名: (2S,3S,4S,6R)-3-[(2S,4R,5S,6R)-4-hydroxy-6-methyl-5-phenylmethoxyoxan-2-yl]oxy-6-methoxy-2,4-dimethyloxan-4-ol
• CAS: 1133161-97-3
• 化学式: C₂₁H₃₂O₇
• 分子量: 396.481
• InChiKey: JGZPAMIKYYEUNZ-ZTYKYNGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->4)-2,6-dideoxy-3-C-methyl-α-L-arabino-hexopyranoside 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以80%的产率得到methyl 4-O-benzyl-2,6-dideoxy-3-O-methyl-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：

  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

文献信息

• 2,3-Anhydrosugars in Glycoside Bond Synthesis. Application to 2,6-Dideoxypyranosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1021/jo900131a

  日期：2009.3.20

  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.