20196-69-4Relevant academic research and scientific papers
1,3:4,6-Di-O-benzylidene-D-mannitol as a source for novel chiral intermediates through regioselective reductive cleavage
Aravind, Appu,Baskaran, Sundarababu
, p. 743 - 745 (2005)
Synthetically useful chiral intermediates have been synthesized starting from 1,3:4,6-di-O-benzylidene-D-mannitol by regioselective reductive cleavage using BF3?Et2O and Et3SiH in high yields.
Synthesis of N-oxyamide-linked neoglycolipids
Chen, Na,Xie, Juan
, p. 10716 - 10721 (2014)
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 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.
supporting information, 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.
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
Cysteine protease inhibitors
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, (2008/06/13)
of the formula (IV): where: R1=R′C(O), R′SO2, R′=a bicyclic, saturated or unsaturated, 8-12 membered ring system containing 0-4 hetero atoms selected from S, O and N, which is optionally substituted with up to four substituents independently selected from groups a), b) and c) below; or R′=a monocyclic, saturated or unsaturated, 5-7 membered ring containing 0-3 hetero atoms selected from S, O and N, which monocyclic ring bears at least one substituent selected from group a) and/or c) and which may optionally bear one or two further substituents selected from group b); R4=H, C1-7-alkyl, Ar-C1-7-alkyl, Ar, C3-7-cycloalkyl; C2-7alkenyl; R3=C1-7-alkyl, C2-C7 alkenyl, C2-C7 alkenyl, C3-7-cycloalkyl, Ar-C1-7-alkyl, Ar; R5=C1-7-alkyl, halogen, Ar-C1-7-alkyl, C1-3-alkyl-CONR3R4 or a bulky amine R6 is H, C1-7-alkyl, Ar-C1-7-alkyl, C1-3-alkyl-SO2-Rix, C1-3-alkyl-C(O)—NHRix or CH2XAr q is 0 or 1 have utility as inhibitors of cysteine proteases such as cathepsin K and falcipain.
Lewis Acid-Catalyzed Deprotection of p-Methoxybenzyl Ether
Bouzide, Abderrahim,Sauvé, Gilles
, p. 1153 - 1154 (2007/10/03)
The p-methoxybenzyl protecting group was readily removed from alcohols and phenols using catalytic amounts of AlCl3 or SnCl2 · 2H2O in the presence of EtSH at room temperature. Under these mild conditions other protecting groups such as methyl and benzyl ethers, p-nitrobenzoyl esters, TBDPS ethers and isopropylidene acetal were unchanged.
Regioselective De-O-benzylation with Lewis Acids
Hori, Hiroshi,Nishida, Yoshihiro,Ohrui, Hiroshi,Meguro, Hiroshi
, p. 1346 - 1353 (2007/10/02)
Simple and highly regioselective de-O-benzylations of poly-O-benzylated monosaccharides and polyols with Lewis acids (SnCl4 and TiCl4) were developed.Spectral studies on intermediates complexes showed that three appropriately situated metal chelating functional groups were necessary for the selective de-O-benzylation.
The Synthesis of (R)-2',3'-Dihydroxypropyl 5-Deoxy-5-dimethylarsinyl-β-D-riboside, a Naturally Occurring Arsenic-Containing Carbohydrate
McAdam, David P.,Perera, Anna M. A.,Stick, Robert V.
, p. 1901 - 1908 (2007/10/02)
The synthesis of the title compound, isolated from the brown kelp (Ecklonia radiata) or the giant clam (Tridacna maxima), is reported.Glycosidation of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribose, either directly with (S)-1,2-di-O-benzylglycerol or via the derived orthoester with (S)-1,2-O-isopropylideneglycerol, led to two fully protected glycerol β-D-ribofuranosides.Subsequent chemical manipulations led to a common intermediate having a free hydroxy group at C 5 of the D-ribose residue.Replacement of this hydroxy group by a chlorine atom allowed the introduction of the dimethylarsinyl group at C 5 in a two-step procedure, and removal of protecting groups provided the natural product.
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.
