p-tolyl 2-O-allyl-3-O-methanesulfonyl-1-thio-β-L-fucopyranoside | 1133159-94-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2-O-allyl-3-O-methanesulfonyl-1-thio-β-L-fucopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-3-hydroxy-2-methyl-6-(4-methylphenyl)sulfanyl-5-prop-2-enoxyoxan-4-yl] methanesulfonate
• CAS: 1133159-94-0
• 化学式: C₁₇H₂₄O₆S₂
• 分子量: 388.506
• InChiKey: ITXMVPIJPZILAC-BYHHXJKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-tolyl 2-O-allyl-3-O-methanesulfonyl-1-thio-β-L-fucopyranoside 、 4-甲氧基氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 以95%的产率得到p-tolyl 2-O-allyl-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
• 作为产物：
  描述：

  p-tolyl 2-O-allyl-1-thio-β-L-fucopyranoside 、 甲基磺酰氯 在 二正丁基氧化锡 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以91%的产率得到p-tolyl 2-O-allyl-3-O-methanesulfonyl-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.