436843-87-7Relevant academic research and scientific papers
An all-cis 3,4-dihydroxy-5-aminopiperidine by a novel route to deoxydiamino sugars
Swaleh, Sauda,Liebscher, Juergen
, p. 2099 - 2100 (1999)
An (L)-diaza-1,6-dideoxytalose 7 as a first example of a new synthetic concept for aminodeoxy sugars by destruction of the 5-membered heterocyclic ring of condensed pyridones derived from natural amino acids and an o-bromo- bromomethyl 5-membered heterocy
New strategy for the synthesis of iminoglycitols from amino acids
Swaleh, Sauda,Liebscher, Juergen
, p. 3184 - 3193 (2007/10/03)
A novel strategy for the enantioselective synthesis of polyhydroxypiperidines, which can be considered as iminoglycitols or 2,6-dideoxyazasugars, was developed. α-Benzolsulfonylamino esters served as a C2N building block while 2-bromo-3-(bromomethyl)oxazoles and -thiazoles contributed a C3-unit to the final piperidine ring. At first a dihydropyridine ring was established via alkylation and bromine-lithium exchange. The keto group of the resulting 5,6-dihydro[1,3]oxazolo- and 5,6-dihydro[1,3]thiazolo[4,5-c]pyridin-7(4H)-ones was reduced and, after alkylation reactions, the azole ring was cleaved, thus providing heteroatom substituents for the target piperdines. Protected 5-amino-3,4-dihydroxy and 5-amino-3-hydroxy-4-thiohydroxypiperdines were obtained in the talose series while Mitsunobu reaction of the intermiediates provided access to the altrose series.
