methyl 2-O-benzoyl-3-bromo-3,6-dideoxy-α-D-altropyranoside | 1133159-28-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzoyl-3-bromo-3,6-dideoxy-α-D-altropyranoside
• 英文别名: [(2S,3R,4R,5R,6R)-4-bromo-5-hydroxy-2-methoxy-6-methyloxan-3-yl] benzoate
• CAS: 1133159-28-0
• 化学式: C₁₄H₁₇BrO₅
• 分子量: 345.19
• InChiKey: IUWMDMKXKPPQBO-HSZBIYQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-O-benzoyl-3-bromo-3,6-dideoxy-α-D-altropyranoside 、 乙酸酐 在 硫酸 作用下， 反应 2.0h， 以65%的产率得到1,4-di-O-acetyl-2-O-benzoyl-3-bromo-3,6-dideoxy-D-altropyranose
  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：

  (3aS,4S,6R,7R,7aS)-4-methoxy-6-methyl-2-phenyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol 在 N-溴代丁二酰亚胺(NBS) 、 calcium carbonate 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以73%的产率得到methyl 2-O-benzoyl-3-bromo-3,6-dideoxy-α-D-altropyranoside
  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