Author/Authors :
Shinkiti Koto، نويسنده , , Motoko Hirooka، نويسنده , , Takako Tashiro، نويسنده , , Motokazu Sakashita، نويسنده , , Masaharu Hatachi، نويسنده , , Takayuki Kono، نويسنده , , Miho Shimizu، نويسنده , , Nahoko Yoshida، نويسنده , , Sayaka Kurasawa، نويسنده , , Natsuko Sakuma، نويسنده , , Sunao Sawazaki، نويسنده , , Akihiro Takeuchi، نويسنده , , Naomi Shoya، نويسنده , , Emi Nakamura، نويسنده ,
Abstract :
Alkyl, cycloalkyl, allyl, 4-pentenyl, and benzyl α-glycosides of maltose, cellobiose, and lactose were prepared (17–77% yield; α/β = 70/30–96/4) via a direct reaction of the free disaccharides with a binary AcBr–AcOH mixture, followed by glycosidation with alcohol using FeCl3 in MeNO2 or CH2Cl2, Zemplén deacetylation, and resolution of the anomeric mixture of glycosides by chromatography. Using MeCN as solvent for the glycosidation step, the corresponding β-biosides were also prepared (16–61% yield; α/β = 25/75–5/95).
Keywords :
?-Glycosidation , Iron(III) chloride , Glycosyl bromide , Disaccharide
