## Abstract The ^1^H and ^19^F NMR spectra of the α‐ and β‐pyranose anomers of 4‐deoxy‐4‐fluoro‐D‐glucose (4FG) and 6‐deoxy‐6‐fluoro‐D‐galactose (6FGA) in methanol‐__d__~4~, DMSO‐__d__~6~, acetone‐__d__~6~ and D~2~O solution are reported. Computer analysis of the ABMX spectra of the CHCH~2~F fragm
Conformational analysis of 6-deoxy-6-fluoro-d-glucopyranose, 6-deoxy-6-fluoro-d-galactopyranose, and 4-deoxy-4-fluro-d-glucopyranose in solution by 1H-n.m.r. spectroscopy
✍ Scribed by Raymond J. Abraham; Eric J. Chambers; Thomas W. Anthony
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- English
- Weight
- 317 KB
- Volume
- 226
- Category
- Article
- ISSN
- 0008-6215
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📜 SIMILAR VOLUMES
## Abstract The conformation of D‐glucopyranose and 6‐deoxy‐6‐fluoro‐D‐glucose (6DFG) in solution, as determined by ^1^H and ^19^F NMR, is reviewed. The ^1^H NMR spectra of α‐ and β‐methyl D‐glucopyranosides and 6DFG in methanol, acetone, DMSO, and aqueous solution were acquired and fully analysed.
Sequential tritylation, benzoylation, and detritylation of methyl 3-deoxy-3fluoro-AD-galactop~~oside gave crystalline methyl 2,4-di-O-benzoyl-3-deoxy-3-~uoro-ED-gala~opyr~oside (9), which was used as the initial nucleophile in the synthesis of the target otigosaccha~de (16). Treatment of 9 with 2,3,
Treatment of 3-0-acetyl-5-deoxy-5-(dimethoxyphosphinyl)-l,2-O-isopropylidene-cr-D-glucofuranose (7) with dihydropyran in the presence of pyridinium ptoluenesulfonate gave the 6-0-(tetrahydropyran-2-yl) derivative in 91% yield. Ring-enlargement of this compound by the known, 2-step procedure gave 5-d