A concise synthesis of the 6-O- and 6'-O-sulfated analogues of the sialyl Lewis X tetrasaccharide.
The octyl glycoside of the sialyl Lewis X tetrasaccharide and its 6-O-sulfated and 6'-O-sulfated analogues were chemically synthesized in a concise manner starting from readily accessible monosaccharide intermediates. The synthesis involved formation of an orthogonally protected tetrasaccharide intermediate from which all three materials were prepared. A selective catalytic hydrogenolysis of four O-benzyl ethers in presence of a 4,6-O-benzylidene group was the key step in the synthetic scheme.
Misra
A K
AK
The Burnham Institute, La Jolla, CA 92037, USA.
Ding
Y
Y
Lowe
J B
JB
Hindsgaul
O
O
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002384:Catalysis; D007202:Indicators and Reagents; D008958:Models, Molecular; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D000080506:Sialyl Lewis X Antigen; D013431:Sulfates / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen; D013431:Sulfates