Glycosyl Alkoxythioimidates as Complementary Building Blocks for Chemical Glycosylation

• Published in: Organic letters Vol. 12; no. 24; pp. 5628 - 5631
• Main Authors: Ranade, Sneha C, Kaeothip, Sophon, Demchenko, Alexei V
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 17.12.2010; Amer Chemical Soc
• Subjects: Alcohols - chemistry; Chemistry; Chemistry, Organic; Glycosylation; Imidoesters - chemistry; Molecular Structure; Physical Sciences; Science & Technology; Sulfhydryl Compounds - chemistry; S-BENZOXAZOLYL GLYCOSIDES; THIOGLYCOSIDES; HIGHLY STEREOSPECIFIC METHOD; POTENT; VERSATILE; O-GLYCOSYLATION; OLIGOSACCHARIDE SYNTHESIS; DONORS; 1,2-CIS-GLYCOSYLATION; PRINCIPLES

It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation experiments in the presence of various promoters....