178977-64-5Relevant articles and documents
Fluoridolysis of 5,6-epoxy carbohydrates: application to the synthesis of 5-fluoro lactosamine and isolactosamine glycosides
Hagena, Tara L.,Coward, James K.
experimental part, p. 781 - 794 (2009/10/10)
The synthesis of 6-selenophenyl derivatives of β-1,3 and β-1,4 disaccharides has been explored for the purpose of extending our epoxide fluoridolysis methodology to the synthesis of 5-fluoro analogues of N-acetyl isolactosamine (isoLacNAc, lacto-N-biose) and N-acetyl lactosamine (LacNAc) glycosides. Successful synthesis of the C-6 selenium-containing disaccharides was achieved via Lewis acid-mediated donor and acceptor substrates, the latter containing a selectively protected C-6 hydroxyl group for ultimate conversion to the desired 6-selenophenyl disaccharides. In contrast, the use of selenium-containing acceptor substrates under a variety of conditions failed to yield the desired selenium-containing disaccharides. Oxidation of the 6-selenophenyl derivatives to the corresponding selenoxides followed by thermal elimination yielded the exocyclic olefins, which were converted to the 5,6-epoxides. Epoxide fluoridolysis yielded the desired target compounds, 5-fluoro β-octyl glycoside analogues of type 1 and type 2 glycans. The newly synthesized fluorine-containing disaccharides have potential application as fucosyltransferase substrates, both for mechanistic studies and in the chemoenzymatic synthesis of fluorine-containing oligosaccharides.
Practical synthesis of sulfated analogs of lactosamine and sialylated lactosamine derivatives
Misra, Anup Kumar,Agnihotri, Geetanjali,Madhusudan, Soni Kamlesh,Tiwari, Pallavi
, p. 191 - 199 (2007/10/03)
A series of β-D-Gal-(1 → 4)-β-D-GlcNAc-octyl, NeuAcα-(2 → 3)-β-D-Gal-(1 → 4)-β-D-GlcNAc-octyl, and their 6-O-sulfated and 6′-O-sulfated analogs (1-6) were synthesized in a concise manner starting from readily accessible monosaccharide intermediates. The syntheses involved formation of an orthogonally protected disaccharide and a trisaccharide from which all six compounds were derived. Copyright
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.
Efficient synthesis of 3'-glycosylated LacNac-based oligosaccharides
Ding, Yili,Fukuda, Minrou,Hindsgaul, Ole
, p. 1903 - 1908 (2007/10/03)
LacNAc-based oligosaccharides, including sialyl-(2→3)-LacNAc, dimeric sialyl-(2→3)-LacNAc, trimeric sialyl-(2→3)-LacNAc, β-glucuronyl-(1→3)- LacNAc, and 3-sulfo-β-glucuronyl-(1→3)-LacNAc, were synthesized efficiently from a single protected LacNAc derivative having both OH-3' and 4' unprotected.
