methyl 4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside | 1133161-23-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: Bz(-4)Oli(b1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Glc1Me；[(2R,3S,4R,6R)-4-hydroxy-6-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-2-methyloxan-3-yl] benzoate
• CAS: 1133161-23-5
• 化学式: C₄₁H₄₆O₁₀
• 分子量: 698.81
• InChiKey: HYJWYVSYVQFZTA-UGYUDRFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  methyl 4-O-benzoyl-2,6-dideoxy-2-p-(tolylthio)-β-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以55%的产率得到methyl 4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  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.