Inter- and intramolecular glycosylation of exo-glycals promoted by metallic Lewis acids.
exo-Glycosyl carbonates were employed for inter- and intramolecular glycosylation reactions. A number of metallic Lewis Acids and solvents were examined to enhance the reactivity. The optimum conditions were found to be the use of AlCl3 in 1-nitropropane. The method was demonstrated to be useful for the intermolecular glycosyl transfer of several nucleophiles, including simple alcohols, sugars, and amino acid derivatives; however, intramolecular glycosylations were not successful.
Hsu
Sheng-Jie
SJ
Institute of Biological Chemistry and Genomics Research Center, Academia Sinica, No. 128 Academia Road Section 2, Nan-Kang, Taipei 11529, Taiwan.
Lin
Hui-Chang
HC
Lin
Chun-Hung
CH
D000475:Alkenes / Q000737:chemistry; D000077410:Aluminum Chloride; D017607:Aluminum Compounds / Q000737:chemistry / Q000494:pharmacology; D002712:Chlorides / Q000737:chemistry / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation / Q000187:drug effects*
D000475:Alkenes; D017607:Aluminum Compounds; D002712:Chlorides; D006027:Glycosides; D000077410:Aluminum Chloride