115457-83-5Relevant articles and documents
SUGAR CHEMISTRY WITHOUT PROTECTING GROUPS: A REGIOSELECTIVE ADDITION OF THE PRIMARY HYDROXYL OF MONOSACCHARIDES TO ALKYLISOCYANATES
Plusquellec, Daniel,Lefeuvre, Martine
, p. 4165 - 4168 (1987)
The primary hydroxyl groups of D-glucose, D-galactose and methyl-α-D-glucoside add selectively to alkylisocyanates, thus affording respectively 6-O-carbamoyl-D-glycopyranoses and methyl-6-O-carbamoyl-α-D-glucopyranosides with high yields (except for galactosyl compounds), the temporary protection of the other hydroxyls of the starting sugars being not necessary in the present case.
CHIMIE DES SUCRES SANS GROUPEMENTS PROTECTEURS-II REACTIONS SELECTIVES D'ADDITION DU D-GLUCOSE, DU D-GALACTOSE ET DE D-GLYCOSYLAMINES A DES HETEROCUMULENES
Plusquellec, Daniel,Roulleau, Fabienne,Lefeuvre, Martine,Brown, Eric
, p. 465 - 474 (2007/10/02)
Alkyl isocyanates reacted with 1.5 equivalent of α-methylglucoside, glucose or galactose in pyridine at room temperature, and selectively gave the corresponding 6-N-alkylcarbamates in good yields.The readily available glucosylamine and lactosylamine (1.5-2 eq.) reacted with alkyl isocyanates and isothiocyanates in polar aprotic solvents (pyridine, NMP or DMF), thus affording good yields of the corresponding N-glycosyl N'-alkyl ureas and thioureas.These new sugar derivatives are non-ionic detergents.