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 | 94820-98-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: benzyl 4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside；Bz(-4)Oli(b1-3)[Bz(-4)]Oli(b)-O-Bn；[(2R,3S,4R,6S)-6-[(2R,3R,4R,6R)-3-benzoyloxy-2-methyl-6-phenylmethoxyoxan-4-yl]oxy-4-hydroxy-2-methyloxan-3-yl] benzoate
• CAS: 94820-98-1
• 化学式: C₃₃H₃₆O₉
• 分子量: 576.643
• InChiKey: MFELQVUVDDQIRZ-WJKRIWRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  benzyl 4-O-benzoyl-2,6-dideoxy-2-(p-tolylthio)-β-D-glucopyranosyl-(1->3)-4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside 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65%的产率得到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
  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

• Synthesis of the E-D-C trisaccharide unit of aureolic acid cytostatics
  作者：Joachim Thiem、Manfred Gerken

  DOI：10.1021/jo00207a009

  日期：1985.4
• 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.