Aromatic O-glycosylation.
Carbohydrates carrying an aromatic aglycon are important natural products and thus key synthetic targets. However, due to the electron-withdrawing properties of aromatic rings, phenols are difficult to glycosylate. This review covers the most common carbohydrate donors used for aromatic O-glycosylation (anomeric acetates, halides, trichloroacetimidates and thioglycosides) as well as some less common donors. The scope of the review is to give practical examples of aromatic O-glycosylations and to offer guidelines for glycosylation of typical aromatic residues. Anomeric acetates or trichloroacetimidates, activated under acidic conditions, are preferred for electron rich aromatic aglycons, while glycosyl halides, activated using basic conditions, are preferred for electron deficient aromatic residues.
Jacobsson
Mårten
M
Organic Chemistry, Lund University, PO Box 124, SE-221 00 Lund, Sweden.
Malmberg
Jesper
J
Ellervik
Ulf
U
D000081:Acetamides; D000085:Acetates / Q000737:chemistry; D001711:Biotransformation; D001965:Bromides / Q000737:chemistry; D002712:Chlorides / Q000737:chemistry; D062845:Chloroacetates; D005459:Fluorides / Q000737:chemistry; D006031:Glycosylation; D010755:Organophosphates / Q000737:chemistry; D016566:Organoselenium Compounds / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D029604:Phytolacca americana / Q000378:metabolism; D011926:Rauwolfia / Q000378:metabolism; D012233:Rhizopus / Q000378:metabolism; D013175:Sporothrix / Q000378:metabolism; D013454:Sulfoxides / Q000737:chemistry; D013691:Tellurium / Q000737:chemistry; D013865:Thioglycosides / Q000737:chemistry; D014238:Trichloroacetic Acid / Q000737:chemistry
D000081:Acetamides; D000085:Acetates; D001965:Bromides; D002712:Chlorides; D062845:Chloroacetates; D010755:Organophosphates; D016566:Organoselenium Compounds; D010636:Phenols; D013454:Sulfoxides; D013865:Thioglycosides; D014238:Trichloroacetic Acid; C009528:trichloroacetamide; D013691:Tellurium; D005459:Fluorides