title: Greatly Accelerated Condensation of d-Mannose Diacetonide with Aqueous Formaldehyde (Formalin).
abstract: Condensation of d-mannose diacetate with aqueous formaldehyde, a long known quaternary center-generating transformation, was reinvestigated to solve the hidden problem of incomplete conversion, a lasting challenge since 1979 despite many previous efforts. The mysterious cause for the retarded transformation was found to be generation of formic acid by a Cannizzaro reaction. By using additional amounts of base, the reaction time was shortened from 48 h to 100 min and the product was readily isolated in 81% yield.
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collective Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Dong-Xing
authors.initials: DX
authors.lastname: Tan
authors.affiliation: Key Laboratory of Green Chemical Technology of College of Heilongjiang Province, School of Chemical and Environmental Engineering, Harbin University of Science and Technology , Harbin 150040, China.
authors.forename: Jun
authors.initials: J
authors.lastname: You
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collective Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Mu-Rong
authors.initials: MR
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Bioorganic and Natural Products Chemistry, Collective Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
authors.forename: Yikang
authors.initials: Y
authors.lastname: Wu