50711-01-8Relevant academic research and scientific papers
Synthesis of α-glycosyl thiols by stereospecific ring-opening of 1,6-anhydrosugars
Zhu, Xiangming,Dere, Ravindra T.,Jiang, Junyan,Zhang, Lei,Wang, Xiaoxia
scheme or table, p. 10187 - 10197 (2012/02/05)
Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of α-glycosyl thiols. All the reactions were highly stereoselective and afforded the α-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding α-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to α-glycosyl thiols of great value was established (Figure presented).
PROSTANOIDS. LVI. USEFUL PROSTAGLANDIN SYNTHONS FROM LEVOGLUCOSAN
Tolstikov, G. A.,Valeev, F. A.,Ibragimova, I. P.,Gaisina, I. N.,Spirikhin, L. V.,Miftakhov, M. S.
, p. 1501 - 1506 (2007/10/02)
(1S,6S,7R,9R)-7,9-Dihydroxy-3-oxabicyclononan-4-one, which is a new chiral synthon for cyclopentanoids, was obtained by intramolecular radical cyclization of methyl 4R,6S-dibenzyloxy-7R-hydroxy-8-acetoxyoct-2E,Z-enoates and subsequent removal of th
THE REGIOSELECTIVITY OF TRIBUTYLTIN ETHER-MEDIATED BENZYLATION OF 1,6-ANHYDRO-β-D-HEXOPYRANOSES
Cruzado, M. Carmen,Martin-Lomas, Manuel
, p. 193 - 200 (2007/10/02)
The benzylation of 1,6-anhydro-β-D-galactopyranose and the manno, allo, altro, gulo, talo, gluco, and ido isomers, using bis(tributyltin) oxide and N-methylimidazole, tetrabutylammonium bromide, tetrabutylammonium iodide, or tetrabutylammonium fluoride as
Regioselective Monoalkylation of Non-protected Glycopyranosides by the Dibutyltin Oxide Method
Haque, Mohammed Ekramul,Kikuchi, Tohru,Yoshimoto, Kimihiro,Tsuda, Yoshisuke
, p. 2243 - 2255 (2007/10/02)
Regioselective monoalkylation of some pento- and hexopyranosides (Me β-L-Ara, Ph α-L-Ara, Me α-D-Xyl, Me β-D-Xyl, Me α-D-Glc, Me β-D-Glc, Me α-D-Gal, Me β-D-Gal, and Me α-D-Man) was examined by using the dibutyltin oxide method without protecting the hydroxyl groups.By this method, alkylation proceeds more or less in the same fashion as reported for acylation (through the formation of cyclic tin intermediates) and selectively activates an equatorial hydroxyl group which has an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary hydroxyl group.However, in some instances the position of activation is different.Various monoalkyl ethers thus prepared were identified by analyses of their carbon-13 nuclear magnetic resonance spectra.Keywords-regioselective monoalkylation; glycopyranoside; dibutyltin oxide; cis-vicinal glycol; benzylation; allylation; methoxymethylation; methylation;13C-NMR
