84730-22-3Relevant articles and documents
Synthesis of protected 4-amino- and 4-azido-3-hydroxy-l-prolines from d-glucose
Kasture, Vijay M.,Kalamkar, Navnath B.,Dhavale, Dilip D.
, p. 2735 - 2738 (2012/11/07)
Differentially protected 4-azido- or 4-amino-3-hydroxy-l-prolines were synthesized in good overall yields (21-31%) from d-glucose. The synthetic strategy involved conversion of d-glucose into 3-[(benzyloxycarbonyl)amino]-3- deoxy-1,2-O-isopropylidene-α-d-glucofuranose, which was subjected to mesylation of the 5- and 6-hydroxy groups and subsequent intramolecular S N2 displacement of the 6-O-mesyl group by the 3-(benzyloxycarbonyl) amino group to give a pyrrolidine ring. The resulting intermediate underwent intermolecular SN2 displacement of the 5-O-mesyl group with sodium azide, hydrolysis of 1,2-acetonide group, treatment with sodium periodate, and Pinnick oxidation to give the required compounds. Georg Thieme Verlag Stuttgart New York.
REDUCTION OF 1,2;5,6-DI-O-ISOPROPYLIDENE-α-D-GLUCOFURANOSE DERIVATIVES WITH LITHIUM ALUMINIUM HYDRIDE; A FACILE SYNTHETIC METHOD FOR 3,6-IMINO DERIVATIVES
Yamada, Masahide,Tachibana, Kohichi,Kuroda, Toshio,Sakakibara, Tohru
, p. 189 - 200 (2007/10/02)
Treatment of 3-acylamido- or alkylimino-3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranose with lithium aluminium hydride in boiling 1,4-dioxane afforded unusual products, namely, 3,6-N-alkylimino-3,6-dideoxy-1,2-O-isopropylidene-α-D-glucofuranose or 6
