A facile protocol for direct conversion of unprotected sugars into phenyl 4,6- O-benzylidene-per- O-acetylated-1,2- trans-thioglycosides

• Published in: Carbohydrate research Vol. 338; no. 2; pp. 199 - 202
• Main Authors: Larsen, Kim, Olsen, Carl Erik, Motawia, Mohammed Saddik
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 20.01.2003; Elsevier
• Subjects: Benzylidenation; Biochemistry & Molecular Biology; Carbohydrates - chemistry; Chemistry; Chemistry, Applied; Chemistry, Organic; Crystallisation; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Methods; Optical Rotation; Phenyl 1-thio-β-glycosides; Physical Sciences; Quick access; Scale up; Science & Technology; Thioglycosides - chemical synthesis; Scale up; Quick access; Crystallisation; Phenyl 1-thio-β-glycosides; Benzylidenation; crystallisation; quick access; phenyl 1-thio-beta-glycosides; scale up; STARCH; benzylidenation; CHEMICAL SYNTHESIS
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/S0008-6215(02)00408-1

A short and practical methodology for conversion of unprotected d-glucose, maltose, cellobiose and lactose into the corresponding phenyl 4,6- O-benzylidine-per- O-acetylated-1,2- trans-thioglycosides is described. The protocol is based on the execution of five reaction steps (bromoacetylation, thiophenolysis under phase transfer catalysis conditions, deacetylation, benzylidenation and acetylation) in one continuous procedure and provides a fast access to the title compounds as pure crystalline products without chromatographic purification. Graphic