A Unique Synthetic Method to Convert a D‐Sugar into 2‐Deoxy‐L‐ribitol Through Carbonyl Translocation. Issue 4 (20th December 2012)

• Record Type: Journal Article
• Authors: Hsu, Nai‐Yun; Chang, Che‐Chien
• Is Part Of: European journal of organic chemistry. Issue 4(2013)
• Page Start: 658
• Page End: 661
• Publication Date: 2012-12-20
• Subjects: Carbohydrates -- Nucleosides -- Radical reactions -- Cyclization -- Fragmentation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201201489
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A unique and highly efficient radical process was developed to prepare 2‐deoxy‐L ‐ribitol. The radical cyclization precursor was prepared over several steps fromD ‐sugars. Radical cyclization followed by fragmentation gave exclusively the desired product, with carbonyl translocation in an acyclic carbohydrate system. The radical process was optimized to avoid the formation of byproducts. The reaction mechanism was studied by the concentration effect, which indicated that both the radical cyclization and the fragmentation steps are relatively rapid. The stereochemistry of the 2‐deoxy‐L ‐ribitol was confirmed by X‐ray crystal structure. By using this synthetic approach, aD ‐sugar derivative could be transformed into 2‐deoxy‐L ‐ribose in a single radical reaction. Abstract : A unique and highly efficient radical process (complete within minutes) was developed to prepare of 2‐deoxy‐L ‐ribitol. Radical cyclization followed by fragmentation gave exclusively the desired product, with carbonyl translocation in an acyclic carbohydrate system. By using this synthetic approach, aD ‐sugar derivative could be transformed into a 2‐deoxy‐L ‐sugar in a single radical reaction.