Synthesis and Application of a 2-[(4-Fluorophenyl)-sulfonyl]ethoxy Carbonyl (Fsec) Protected Glycosyl Donor in Carbohydrate Chemistry

被引：1

作者：

Spjut, Sara ^{[1
]}

Qian, Weixing ^{[1
]}

Elofsson, Mikael ^{[1
]}

机构：

[1] Umea Univ, Dept Chem, SE-90187 Umea, Sweden

来源：

MOLECULES | 2010年 / 15卷 / 08期

关键词：

base sensitive protecting group; O-protection; glycoconjugate synthesis; glycosylation; SOLID-PHASE SYNTHESIS; F-19; NMR-SPECTROSCOPY; OLIGOSACCHARIDE SYNTHESIS; LINKER; FMOC; TSC;

D O I：

10.3390/molecules15085708

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The 2-[(4-fluorophenyl)sulfonyl] ethoxy carbonyl (Fsec) group for protection of hydroxyl groups has been designed, synthesized, and evaluated. Fsec-Cl was readily prepared in 91% yield over three steps and subsequently used to protect 4-fluorobenzyl alcohol in high yield. The Fsec group was cleaved from the resulting model compound under mild basic conditions e. g., 20% piperidine in DMF and was stable under acidic conditions, e. g., neat acetic acid. The Fsec group was used to protect the unreactive 4-OH in a galactose building block that was later used in the synthesis of 6-aminohexyl galabioside.

引用

页码：5708 / 5720

页数：13

共 23 条

[1] Methylsulfonylethoxycarbonyl (Msc) and fluorous propylsulfonylethoxycarbonyl (FPsc) as hydroxy-protecting groups in carbohydrate chemistry [J].