Asymmetric Synthesis of 1,3,6-Trideoxy-3,6-difluoronojirimycin1
Titel:
Asymmetric Synthesis of 1,3,6-Trideoxy-3,6-difluoronojirimycin1
Auteur:
Lee, C.-Kuan Jiang, Huixin
Verschenen in:
Journal of carbohydrate chemistry
Paginering:
Jaargang 14 (1995) nr. 3 pagina's 407-416
Jaar:
1995-04-01
Inhoud:
Reaction of 5-azido-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose (1) with trifluoromethanesulfonic anhydride followed by tris(dimethylamino)sulfonium difluorosilicate gave a 1:2 mixture of 5-azido-3,5,6-trideoxy-3-fluoro-1,2-O-isopropylidene-α-D-xylohex-5-enofuranose (2) and 5-azido-3,5,6-trideoxy-3,6-difluoro-α-D-glucofuranose (3) in 74% yield. When 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose (7) was similarly treated, it yielded instead, 5-azido-5-azido-3-O-trifluoromethanesulfonyl-1,2-O-isopropylidene-α-D-ribo-hex-5-enofuranose (8). Further treatment of 8 with TASF gave 2. The 3-O-benzoate 4 also did not yield the expected product, but instead, gave 5-azido-6-O-benzoyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose (5). Deacetalation and hydrogenation of 3 gave 1,3,6-trideoxy-3,6-difluornojirimycin [(2S,3R,5S)-4-fluoro-3,5-dihydroxy-2-fluoromethylpiperidine] (10).
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