Carbohydrate Research p. 33 - 44 (1994)
Update date:2022-08-02
Topics:
Bennis, Khalil
Calinaud, Pierre
Gelas, Jacques
Ghobsi, Mebrouk
D-Ribono-1,4-lactone, after acetalation, tritylation, and reduction, leads to a cyclization compound which gave with tosyl chloride 1,4-anhydro-2,3-O-isopropylidene-5-O-trityl-D-ribitol.The latter was transformed (acid hydrolysis, periodate oxidation, reduction, tritylation, and tosylation) into a ditosylated derivative 16, which was cyclized into morpholines by the action of primary amines.Acid hydrolysis, followed by acetylation, gives the (2S)-acetoxymethyl-4-isopropyltetrahydro-1,4-oxazine (21).A similar sequence has been applied to D-gulonolactone to give access to oxazines 33, 34, and 35. Keywords: Synthesis; D-Ribono-1,4-lactone; D-Gulono-1,4-lactone; Morpholine derivatives
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