Three alternative protocols were developed to carry out the selective installation of acetal groups on carbohydrates and polyols under mildly acidic, solvent-free conditions. One protocol is based on a diol/aldehyde condensation at room temperature, with an acetolysis process serving for the activation of the carbonyl component. A second approach is based on an orthoester-mediated activation of the carbonyl component at high temperature. The third protocol is instead entailing a transacetalation mechanism. Combination of these methods allows a wide set of acetal-protected building blocks to be accessed in short times under very simple experimental conditions working under air. The scope of the latter two approaches was also extended to unusual one-pot synthetic sequences leading to concomitant Fischer glycosidation/acetal protection of reducing sugars.

Three Solvent-Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One-Pot Generation of Orthogonally Protected Building Blocks / Traboni, Serena; Bedini, Emiliano; Giordano, Maddalena; Iadonisi, Alfonso. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 357:(2015), pp. 3562-3572. [10.1002/adsc.201500745]

Three Solvent-Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One-Pot Generation of Orthogonally Protected Building Blocks

TRABONI, SERENA;BEDINI, EMILIANO;IADONISI, ALFONSO
2015

Abstract

Three alternative protocols were developed to carry out the selective installation of acetal groups on carbohydrates and polyols under mildly acidic, solvent-free conditions. One protocol is based on a diol/aldehyde condensation at room temperature, with an acetolysis process serving for the activation of the carbonyl component. A second approach is based on an orthoester-mediated activation of the carbonyl component at high temperature. The third protocol is instead entailing a transacetalation mechanism. Combination of these methods allows a wide set of acetal-protected building blocks to be accessed in short times under very simple experimental conditions working under air. The scope of the latter two approaches was also extended to unusual one-pot synthetic sequences leading to concomitant Fischer glycosidation/acetal protection of reducing sugars.
2015
Three Solvent-Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One-Pot Generation of Orthogonally Protected Building Blocks / Traboni, Serena; Bedini, Emiliano; Giordano, Maddalena; Iadonisi, Alfonso. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - 357:(2015), pp. 3562-3572. [10.1002/adsc.201500745]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/612293
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