p-tolyl 3,4-anhydro-1-thio-β-L-fucopyranoside | 1133159-69-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: p-tolyl 3,4-anhydro-1-thio-β-L-fucopyranoside
• 英文别名: (1R,2S,4R,5S,6S)-2-methyl-4-(4-methylphenyl)sulfanyl-3,7-dioxabicyclo[4.1.0]heptan-5-ol
• CAS: 1133159-69-9
• 化学式: C₁₃H₁₆O₃S
• 分子量: 252.334
• InChiKey: SEUFQTXIEVKCSH-AHRFKUBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  4

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 3-O-methanesulfonyl-1-thio-β-L-fucopyranoside	1133159-57-5	C14H20O6S2	348.441

反应信息

• 作为产物：
  描述：

  p-tolyl 3-O-methanesulfonyl-1-thio-β-L-fucopyranoside 、 sodium methylate 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 以5%的产率得到p-tolyl 2,3-anhydro-6-deoxy-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

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.