De novo synthesis of carbohydrates. Part 14. Preparation of 4-aminolyxose derivatives. X-Ray molecular structure of ethyl 6-ethoxycarbonylamino-8-hydroxymethyl-3,3-dimethyl-2,4-dioxa-7-azabicyclo[3.3.0]octane-7-carboxylate

Abstract

The synthesis of racemic 4-aminolyxose derivatives was carried out via the Diels–Alder adduct of diethyl azodicarboxylate and 5-methoxypenta-1,4-dien-1-ol. The N–N bond in the highly functionalised hexahydropyridazine intermediate (10) was successfully cleaved using sodium in liquid ammonia. The relative stereochemistry of the product 4-aminopentose derivative was determined by X-ray methods.