Application of a phase transfer reaction to the synthesis of l-fructose

✍ Scribed by Yonas Gizaw; James N. BeMiller

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 277 KB
• Volume: 266
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(94)00255-e

✦ Synopsis

L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-cr-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O-(p-tolylsulfonyl)-a-L-sorbopyranose (3). Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-a-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).