20258-50-8Relevant academic research and scientific papers
A latent reactive handle for functionalising heparin-like and LMWH deca- and dodecasaccharides
Miller, Gavin J.,Broberg, Karl. R.,Rudd, Claire,Helliwell, Madeleine R.,Jayson, Gordon C.,Gardiner, John M.
, p. 11208 - 11219 (2015/11/27)
d-Glucosamine derivatives bearing latent O4 functionality provide modified H/HS-type disaccharide donors for a final stage capping approach enabling introduction of conjugation-suitable, non-reducing terminal functionality to biologically important glycosaminoglycan oligosaccharides. Application to the synthesis of the first O4-terminus modified synthetic LMWH decasaccharide and an HS-like dodecasaccharide is reported.
Synthesis of N-oxyamide-linked neoglycolipids
Chen, Na,Xie, Juan
, p. 10716 - 10721 (2015/02/19)
N-Oxyamide-containing compounds have shown improved metabolic stability and interesting secondary structures due to the good hydrogen bond-donating property of N-oxyamide. β-Glucolipids linked by the N-oxyamide bond have been successfully synthesized as novel mimics of glycoglycerolipids and glycosphingolipids.
A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin
Kadota, Isao,Abe, Takashi,Uni, Miyuki,Takamura, Hiroyoshi,Yamamoto, Yoshinori
, p. 3643 - 3647 (2008/09/20)
Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring.
1,2,5,6-Tetra-O-benzyl-D-mannitol derivatives as novel HIV protease inhibitors
Bouzide, Abderrahim,Sauve, Gilles,Sevigny, Guy,Yelle, Jocelyn
, p. 3601 - 3605 (2007/10/03)
The synthesis and structure-activity relationships of HIV protease inhibitors derived from carbohydrate alditols are discussed. We disclose a new series of 1,2,5,6-tetra-O-alkyl-D-mannitol exhibiting sub-micromolar activity against HIV-protease. This seri
Highly selective Silver(I) oxide mediated monoprotection of symmetrical diols
Bouzide, Abderrahim,Sauve, Gilles
, p. 5945 - 5948 (2007/10/03)
Treatment of symmetrical diol with Ag2O and alkyl halide gave the monoprotected derivative in good to excellent yield.
Benzylation of sugar polyols by means of the PTC method
Szeja, W.,Fokt, I.,Grynkiewicz, G.
, p. 224 - 226 (2007/10/02)
Studies on benzylation of hydrophilic carbohydrate derivatives with benzyl chloride, using a phase-transfer technique, have led to the conclusion that alkylation of a substrate can be greatly facilitated by the introduction of a "co-catalyst" (e.g. a tertiary alcohol) and/or a co-solvent (e.g.DMSO) to the reaction mixture.Efficient procedures for benzylation of sugar derivatives having three to eight hydroxyl groups per molecule, in two-phase system employing an almost stoichiometric amount of the alkylating agent, are presented.
SYNTHESIS OF PHOSPHATIDYL-β-GLUCOSYL GLYCEROL CONTAINING A DIOLEOLYL DIGLYCERIDE MOIETY. APPLICATION OF THE TETRAISOPROPYLDISILOXANE-1,3-DIYL (TIPS) PROTECTING GROUP IN SUGAR CHEMISTRY. PART IV
Boeckel, C. A. A. van,Visser, G. M.,Boom, J. H. van
, p. 4557 - 4566 (2007/10/02)
The preparation of phosphatidyl-β-glucosyl diglyceride 12c is described.The synthesis of glycophospholipid 12c was accomplished by using: (a) the levulinoyl group for the temporary protection of the glucose hydroxyl functions of 6b, which could then be converted into the dioleoyl substituted derivative 7c; (b) the tetraisopropyldisiloxane-1,3-diyl (TIPS) group to protect the 3'- and 4'-hydroxyl groups of 7c, in a two step procedure, to afford compound 8; (c) a 2,4-dichlorophenyl protected phosphatidic acid derivative 11.Compound 11 could be selectively coupled to the primary hydroxyl function of 8 to afford the fully protected glycophospholipid 12a.Finally, removal of the 2,4-dichlorophenyl and TIPS protecting groups from 12a was performed with syn-4-nitrobenzaldoximate and fluoride ions, respectively, to afford glycophospholipid 12c.
