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18.16.3 Product Subclass 3: Orthocarbamic Acid Triesters

DOI: 10.1055/sos-SD-018-01407

Diaper, C. M.Science of Synthesis, (2005181212.

Orthocarbamic acid triesters are generally referred to as carbamate acetals. Simple carbamate acetals and trioxaazaspirans are acid sensitive. They are usually purified by distillation or recrystallization. This reactivity has led to research into their use as pro-drugs in drug delivery systems.[‌108‌] Heterocyclic carbamate acetals such as 2,2-dialkoxy-substituted dihydrooxadiazoles and 2,5-dihydrooxazoles have been reported. They are generally more stable than the acyclic derivatives and can in some cases be purified by flash chromatography. Amide derivatives such as 3C12-tris-C10N+, however, are sufficiently stable to be used in the construction of synthetic bilayer membranes.[‌109‌]