Facile and regioselective preparation of partly O-benzylated D-glucopyranose acetates via acid-mediated simultaneous debenzylation-acetolysis.
Fully O-benzylated methyl alpha-D-glucopyranoside shows a steady order in stepwise debenzylation when it is treated with sulfuric acid in acetic anhydride. Based on the order of debenzylation, regioselective preparations of 2,3,4-tri-, 2,3-, 2,4-, 3,4-di-, and 2-O-benzyl-D-glucopyranose acetates were facilitated in greater than 80% yields. The key points of the preparative reactions were the control of the acid strength and choice of suitable substrates.
Cao
Yang
Y
School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan.
Okada
Yasunori
Y
Yamada
Hidetoshi
H
D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D000089:Acetic Anhydrides / Q000737:chemistry; D000143:Acids / Q000737:chemistry*; D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000085:Acetates; D000089:Acetic Anhydrides; D000143:Acids; D001593:Benzyl Compounds; D006027:Glycosides