p-tolyl 3-O-methanesulfonyl-4-O-(p-methoxybenzyl)-1-thio-β-L-fucopyranoside | 1133160-08-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 3-O-methanesulfonyl-4-O-(p-methoxybenzyl)-1-thio-β-L-fucopyranoside
• 英文别名: [(2S,3R,4S,5S,6R)-5-hydroxy-3-[(4-methoxyphenyl)methoxy]-2-methyl-6-(4-methylphenyl)sulfanyloxan-4-yl] methanesulfonate
• CAS: 1133160-08-3
• 化学式: C₂₂H₂₈O₇S₂
• 分子量: 468.592
• InChiKey: ZRGFLMNGKQZJQR-JHAAVKQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  8

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	p-tolyl 2-O-allyl-3-O-methanesulfonyl-4-O-(p-methoxybenzyl)-1-thio-β-L-fucopyranoside	1133160-01-6	C25H32O7S2	508.657

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	p-tolyl 2,3-anhydro-6-deoxy-4-O-(p-methoxybenzyl)-1-thio-β-L-gulopyranoside	1133159-17-7	C21H24O4S	372.485

反应信息

• 作为反应物：
  描述：

  p-tolyl 3-O-methanesulfonyl-4-O-(p-methoxybenzyl)-1-thio-β-L-fucopyranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 5.0h， 以90%的产率得到p-tolyl 2,3-anhydro-6-deoxy-4-O-(p-methoxybenzyl)-1-thio-β-L-gulopyranoside
  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：

  p-tolyl 2-O-allyl-3-O-methanesulfonyl-4-O-(p-methoxybenzyl)-1-thio-β-L-fucopyranoside 在 四(三苯基膦)钯 、 溶剂黄146 作用下， 反应 48.0h， 以88%的产率得到p-tolyl 3-O-methanesulfonyl-4-O-(p-methoxybenzyl)-1-thio-β-L-fucopyranoside
  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.