Syntheses of Lewis(x) and dimeric Lewis(x): construction of branched oligosaccharides by a combination of preactivation and reactivity based chemoselective one-pot glycosylations.
Two asymmetrically branched oligosaccharides, LewisX and dimeric LewisX, were assembled in one pot with high yields and exclusive regio- and stereoselectivities. p-Tolyl thioglycosides were utilized as the sole type of building blocks, thus simplifying the overall synthetic design. The reactivity-independent nature of the preactivation based method allows modular assembly of the dimeric LewisX octasaccharide without the need for tedious protective group manipulation to achieve exact anomeric reactivities.
Miermont
Adeline
A
Department of Chemistry, The University of Toledo, Toledo, OH 43606, USA.
Zeng
Youlin
Y
Jing
Yuqing
Y
Ye
Xin-shan
XS
Huang
Xuefei
X
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D020650:Combinatorial Chemistry Techniques; D006031:Glycosylation; D007983:Lewis Blood Group Antigens; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry
D007983:Lewis Blood Group Antigens; C494219:Lewis a oligosaccharide; D009844:Oligosaccharides