63598-36-7Relevant academic research and scientific papers
Synthetic heparin pentasaccharides
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Page/Page column 27; 32; 53, (2016/02/12)
Preparation and use of synthetic monosaccharides, disaccharides, trisaccharides, tetrasaccharides and pentasaccharides useful for the preparation of synthetic heparinoids.
A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction
Xing, Shuo,Gleason, James L.
, p. 1515 - 1520 (2015/01/30)
A novel synthetic route leading to N-glycolyl muramyl dipeptide (MDP), a bacterial glycopeptide of particular interest in studies of nucleotide-binding oligomerization domain-containing protein 2 (NOD2), is described. The synthetic strategy hinges on the alkylation of benzylidene-protected glucal with 2-bromopropionic acid and thus circumvents a challenging and non-reproducible SN2 step at the C-3 position of glucosamine derivatives. The subsequent sequence includes an azidonitration and an unusual azide reduction/acylation step via an aza ylide/oxaphospholidine intermediate. This approach generates a protected N-glycolyl MDP that can be either subjected to a one-step global deprotection or differentially deprotected to obtain further derivatives.
A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides
Balmond, Edward I.,Benito-Alifonso, David,Coe, Diane M.,Alder, Roger W.,McGarrigle, Eoghan M.,Galan, M. Carmen
supporting information, p. 8190 - 8194 (2014/08/18)
A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.
A facile synthesis of 4,6-O-benzylidene-d-glycals via 1,5-anhydro-4,6-O-benzylidene-d-hex-1-en-3-ulose
Sakakibara, Tohru,Ito, Tsubasa,Kotaka, Chika,Kajihara, Yasuhiro,Watanabe, Yuhya,Fujioka, Aki
experimental part, p. 2740 - 2743 (2009/04/11)
Benzylidenation of readily available 1,5-anhydro-d-hex-1-en-3-ulose, followed by sodium borohydride reduction, afforded the title compounds in high yields. Separation of 4,6-O-benzylidene-d-allal and -d-glucal was accomplished by selective acetylation wit
Synthesis of saponins with cholestanol, cholesterol, and friedelanol as aglycones
Schimmel, Joerg,Eleuterio, M. Ines Passos,Ritter, Gerd,Schmidt, Richard R.
, p. 1701 - 1721 (2007/10/03)
Procedures for the synthesis of branched Xylss(1→3)[Galss- (1→2)]-Glc and Xylss(1→3)[Galss(1→2)]-GlcUA trisaccharides ss-linked to the 3-O of cholesterol, cholestanol, and friedelanol, respectively, were developed. To this end, ss-selective glucosylation
A new entry to 4,6-O-benzylidene glucal from phenyl 1-seleno-α-d- mannopyranoside
Osborn, Helen M.I.,Meo, Paul,Nijjar, Rajdeep K.
, p. 1935 - 1937 (2007/10/03)
The two-step synthesis of 4,6-O-benzylidene glucal, in 59% overall yield, from phenyl 1-seleno-α-d-mannopyranoside is described.
A facile synthesis of 4,6-O-benzylidene glucal
Chambers, David J.,Evans, Graham R.,Fairbanks, Antony J.
, p. 1767 - 1769 (2007/10/03)
4,6-O-Benzylidene protected D-glucal, a useful synthetic intermediate, may be accessed from the extremely cheap and readily available starting material α-methyl glucopyranoside, via a simple four-step reaction sequence involving selective triflation and iodide displacement at C-2.
Silylmethylene radical cyclization. A stereoselective approach to branched sugars
Pedretti, Valerie,Mallet, Jean-Maurice,Sinay, Pierre
, p. 247 - 258 (2007/10/02)
Ethyl 6-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (2) was converted, in three steps and in 73percent overall yield, into ethyl 6-O-benzyl-2,3-dideoxy-3-C-(hydroxymethyl)-α-D-ribo-hex-2-enopyranoside.This transformation involved silylation of 2
Reaction of 4,6-O-Benzylideneglycals with Benzoic Acid, Triphenylphosphine, and Diethyl Azodicarboxylate and of the Products with Sodium Methoxyde. X-Ray Structure of 1-O-Benzoyl-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranose, C21H22O6
Guthrie, R. D.,Irvine, Robert W.,Davison, Bruce E.,Henrick, Kim,Trotter, Jill
, p. 468 - 472 (2007/10/02)
Reaction of 4,6-O-benzylidene-D-allal with benzoic acid, triphenylphosphine, and diethyl azodicarboxylate gave a mixture of 1-O-benzoyl-4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranose (3) as the major product together with its β-anomer (4) and 3-O-benzoyl-4,6-O-benzylidene-D-glucal (5).Debenzoylation led to a mixture of the 4,6-O-benzylidene-D-glucal, 4,6-O-benzylidene-2-deoxy-3-O-methyl-D-arabino- and -D-ribo-hexopyranose.The structure of the arabino-isomer (6) was established by X-ray analysis of its 1-O-benzoyl derivative.Crystals are orthorhombic, space group P212121, a=21.789(2), b=14.772(3), c=5.925(2) Angstroem.The structure was solved by direct methods and refined to R 0.095.
