Fluorination with F/sub 2/. A convenient synthesis of 2-deoxy-2-fluoro-D-glucose

Journal Article · Sat Jan 01 04:00:00 UTC 1977 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00433a037· OSTI ID:5378286

Ido, T; Wan, C N; Fowler, J S; Wolf, A P

A method is described for the direct conversion of 3,4,6-tri-0-acetyl-D-glucal to 3,4,6-tri-0-acetyl-2-deoxy-2-fluoro-..cap alpha..-D-glucopyranosyl fluoride (I) and 3,4,6-tri-0-acetyl-2-deoxy-2-fluoro-..beta..-D-mannopyranosyl fluoride (II) by reaction with F/sub 2/. I and II hydrolyze to 2-deoxy-2-fluoro-D-glucose and 2-deoxy-2-fluoro-D-mannose. The method can be used to prepare I and II in yields of 35 and 26%, respectively. (BLM)

• Research Organization: Brookhaven National Lab., Upton, NY
• OSTI ID: 5378286
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 42:13; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALDEHYDES
CARBOHYDRATES
CHEMICAL PREPARATION
CHEMICAL REACTIONS
FLUORINATION
GLUCOSE
HALOGENATION
HEXOSES
MANNOSE
MONOSACCHARIDES
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
SACCHARIDES
SYNTHESIS