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An efficient and highly regioselective synthesis of 4-deoxy- and 2-acetamido-2,4-dideoxy-β-d-threo-hex-3-enopyranosides

✍ Scribed by Emanuele Attolino; Giorgio Catelani; Felicia D'Andrea

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
82 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

The preparation of the previously undescribed class of 4-deoxy-and 2,4-dideoxy-2-acetamido-b-D-threo-hex-3-enopyranosides was accomplished with a very high yield and a complete regioselectivity by means of a simultaneous activation-elimination process of the OH-4 group of b-D-talopyranosides (5a,b) and 2-acetamido-2-deoxy-b-D-talopyranosides (5c,d) with NaH/N,N%-sulfuryldiimidazole. The same reaction of analogous b-D-galactopyranosides (5e,f) is not regioselective, leading to mixtures of 3-and 4-hexeno derivatives. This difference is evidently determined by the orientation of the C-2 substituent, which, in the talo series, is anti diaxially disposed to the H-3 eliminating group.

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