160242-99-9Relevant academic research and scientific papers
A novel, readily accessible lactosaminyl donor: N-Trichloroethoxycarbonyl-hexa-O-benzoyl-β-D-lactosaminyl fluoride
Kaji,Lichtenthaler,Osa,Zen
, p. 1172 - 1179 (2007/10/02)
A simple, preparatively satisfactory 10-step sequence is described for converting lactose into a novel, suitably blocked lactosaminyl donor: N-Trichloroethoxycarbonyl-β-D-lactosaminyl fluoride (5). The key intermediate in this conversion is the particularly well-accessible oxime of lactosulosyl bromide (52% for the 6 steps from lactose), which on α-glycosidation with p-methoxybenzyl alcohol, oxime reduction, N-protection by Troc chloride, and the anomeric fluorination yields 5 (37% for the 4 steps). The utility of 5 as an effective donor was proved by the β-selective glycosylation of the primary 6-OH of 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (14) and the 3-OH of methyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside (16), both affording the respective trisaccharides 15 and 18 in high yields. The latter, when subjected to N-deprotection, N-acetylation, and de-O-acylation gave, in 42% yield based on donor 5, β-D-Gal-(1 → 4)-β-D-GlcNAc-(1 → 3)-β-D-Gal-(1 → Me), a core trisaccharide unit of immunologically important carbohydrate antigens.
Synthesis of the 5-aminopentyl glycoside of β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-L-Fucp and fragments thereof related to glycopeptides of human Christmas factor and the marine sponge Microciona prolifera
Ziegler, Thomas
, p. 195 - 212 (2007/10/02)
The marine sponge Microciona prolifera and human coagulation factor IX (Christmas factor)-related mono- to tri-saccharide 5-aminopentyl glycosides β-D-Galp-R (5), β-D-GlcpNAc-R (16), β-D-Galp-(1->4)-β-D-GlcpNAc-R (26), β-D-GlcpNAc-(1->3)-β-L-Fucp-R (39), β-D-GlcpNAc-(1->3)-α-L-Fucp-R (43), β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-β-L-Fucp-R (45), and β-D-Galp-(1->4)-β-D-GlcpNAc-(1->3)-α-L-Fucp-R (47), where R is a 5-aminopentyloxy spacer moiety, which allowed the construction of glycoconjugates, were prepared.Thus 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate (10) and 1,3,4,6-tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose (13) were condensed with N-Z-protected 5-aminopentanol (2) followed by conversion of the coupling products into the corresponding N-acetylglucosamine derivatives, to give compound 16 after deblocking.Similarly, the donors 10 and 13 were coupled to position 3 of suitably protected aminopentyl β- (32) and α- (37) -L-fucopyranosides, to give the disaccharides 39 and 43, respectively.Starting from lactose, O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl trichloroacetimidate (23) was prepared and used as an efficient disaccharide donor for the construction of ligand 26 from 2 and of the trisaccharide ligands 45 and 47 from fucosides 32 and 37, respectively.Key words: Christmas factor, human; Coagulation factor IX; Human marine sponge Microciona prolifera; Aminopentyl glycoside
