Derivatives of 2-hydroxy-1,4-oxathiane and 2-hydroxymorpholine. A new class of sugar☆

Add time:08/21/2019    Source:sciencedirect.com

Application in sequence of periodate oxidation, borohydride reduction, tosylation, and treatment with sodium sulphide to methyl α-l-rhamnopyranoside affords (2R,6S)-2-methoxy-6-methyl-1,4-oxathiane. Likewise, methyl 6-O-trityl-α-d-glucopyranoside and 1,6-anhydro-β-d-glucopyranose were converted into 1,4-oxathiane derivatives. Acid-catalysed equilibration of (2R,6S)-2-methoxy- and (2R,6S)-2-acetoxy-6-methyl-1,4-oxathiane affords, in each case and in contrast to structurally related tetrahydropyran derivatives, a mixture containing ca. 70% of the cis (diequatorial) isomer.Replacement of sodium sulphide by methanolic ammonia in the above reaction sequence results in the conversion of the rhamnoside into (2R,6S)-2-methoxy-6-methylmorpholine. The behaviour of the free amine and the N-acetyl derivative on acid hydrolysis is described. At low temperature, the n.m.r. spectrum of the N-acetyl derivative is consistent with the existence of geometrical isomers.

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