115414-47-6Relevant articles and documents
Synthesis of β-glycosides of N-acetylglucosamine in the presence of HgI2
Zemlyakov,Kur'yanov,Chirva
, p. 352 - 355 (1996)
The use of HgI2 as catalyst in the synthesis of trans-glycosides of N-acetylglucosamine is described. Using this catalyst, β-glycosides of N-acetylglucosamine with aglycons of different structures and lyophilicities have been synthesized. The p
Synthesis of oligosaccharides designed to form micelles, corresponding to structures found in ovarian cyst fluid
Buskas, Therese,Konradsson, Peter
, p. 25 - 51 (2007/10/03)
The syntheses of α-D-GlcpNAc-(1 →4)-β-D-Galp-(1→4)-β-D-GlcNAc-(1→O)-(CH2)15CH3 (1) and fragments thereof, corresponding to structures found in human ovarian cyst fluid, are described. Silver triflate promoted coupling of 3.4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl bromide (12) and galactose acceptor (11) gave a disaccharide donor (13), which was readily transformed into the corresponding bromoderivative 18. For the synthesis of disaccharide β-D-Galp-(1 →4)-D-GlcNAc, several differently protected glucosamine acceptors were prepared. It was found that cetyl alcohol needed to be introduced after the formation of the β-galactoside bond. Glycosylation of pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (30) with (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1 →4)-2,3,6-tri-O-benzoyl-α-D-galactopyranosyl bromide (18) by use of silver triflate as promoter gave the desired trisaccharide 31. Finally 31 was transformed via coupling to the long alkyl chain aglycon and deprotection into the title compound 1.
