p-tolyl 2-O-allyl-1-thio-β-L-fucopyranoside | 1133159-85-9

• 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-1-thio-β-L-fucopyranoside
• 英文别名: (2S,3S,4R,5S,6R)-2-methyl-6-(4-methylphenyl)sulfanyl-5-prop-2-enoxyoxane-3,4-diol
• CAS: 1133159-85-9
• 化学式: C₁₆H₂₂O₄S
• 分子量: 310.414
• InChiKey: WIWOCZUTIPPRBL-BPKBQXTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以4.20 g的产率得到p-tolyl 2-O-allyl-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

• One-Pot Regioselective Diacylation of Pyranoside 1,2-<i>cis</i> Diols
  作者：Taeok Kim、Michael R. Bell、V. Narasimharao Thota、Todd L. Lowary

  DOI：10.1021/acs.joc.2c00252

  日期：2022.4.1

  A one-pot strategy for functionalizing pyranoside 1,2-cis-diols with two different ester protecting groups is reported. The approach employs regioselective acylation via orthoester hydrolysis promoted by a carboxylic acid, e.g., levulinic acid, acetic acid, benzoic acid, or chloroacetic acid. Upon removal of water and introduction of a coupling agent, the carboxylic acid is esterified to the hydroxyl

  报道了一种用两种不同的酯保护基团对吡喃糖苷 1,2-顺式二醇进行功能化的一锅法。该方法通过由羧酸例如乙酰丙酸、乙酸、苯甲酸或氯乙酸促进的原酸酯水解使用区域选择性酰化。在除去水并引入偶联剂后，羧酸酯化为水解过程中释放的羟基。虽然适用于吡喃糖苷支架上的 1,2-顺式二醇，但该方法应适用于任何六元环上的此类基序。
• 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.