124579-04-0Relevant articles and documents
Reactions of phenyl and ethyl 2-O-sulfonyl-1-thio-α-d-manno- and β-d-glucopyranosides with thionucleophiles
Liptak, Andras,Lazar, Laszlo,Borbas, Aniko,Antus, Sandor
experimental part, p. 2461 - 2467 (2010/03/03)
Persubstituted derivatives of phenyl and ethyl 2-O-sulfonyl-1-thio-α-d-manno- and β-d-glucopyranosides were synthesized and reacted either with PhSNa or with MeSNa. The phenyl-1-thio compounds afforded the dithio-1,2-cis-axial/equatorial-α-d-glucopyranosi
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
Efficient methods for glycosidations with glycals - A key intermediate for the synthesis of mucin core 1-type O-glycan
Geiger, Jürgen,Barroca, Nadine,Schmidt
, p. 836 - 840 (2007/10/03)
The use of glycals as acceptors in glycosylation reactions is hampered by their sensitivity to acids. We report here on the successful use of mild Lewis acid [Sn(OTf)2] as catalyst for the glycosylation with O-glycosyl trichloroacetimidates and on the development of this method to construct a key intermediate for the synthesis of mucin type O-glycans. To this end, chemoselective nitration of O-glycosylated glycals, stereoselective threonine addition, and reduction of the nitro group to the amino group by an efficient procedure avoiding the use of an expensive catalyst was performed.
A NOVEL 1,3 O -> C SILYL REARRANGEMENT IN CARBOHYDRATE CHEMISTRY: SYNTHESIS OF α-D-GLYCOPYRANOSYLTRIMETHYLSILANES
Pedretti, Valerie,Veyrieres, Alain,Sinay, Pierre
, p. 77 - 88 (2007/10/02)
Reductive lithiation of 2-O-trimethylsilyl derivatives of phenyl thiogluco and -galactopyranosides gives rise to a 1,3 O -> C silyl migration leading to α-D-gluco and -galactopyranosyltrimethylsilanes in good yields.The expected β-elimination is observed
PREPARATION OF PYRANOID GLYCAL DERIVATIVES FROM PHENYL THIOGLYCOSIDES AND GLYCOSYL PHENYL SULPHONES
Fernandez-Mayoralas, Alfonso,Marra, Alberto,Trumtel, Michel,Veyrieres, Alain,Sinay, Pierre
, p. 81 - 96 (2007/10/02)
Phenyl thioglycopyranosides with various protecting groups (acetal, ether, ester) underwent reductive lithiation at C-1, followed by rapid elimination of the 2-substituent, when treated with lithium naphthalenide in tetrahydrofuran at low temperature.Thus
CONVENIENT SYNTHESES OF SUBSTITUTED PYRANOID GLYCALS FROM THIOPHENYL GLYCOSIDES AND GLYCOSYL PHENYLSULFONES
Fernandez-Mayoralas, Alfonso,Marra, Alberto,Trumtel, Michel,Veyrieres, Alain,Sinay, Pierre
, p. 2537 - 2540 (2007/10/02)
A series of substituted thiophenyl glycosides and glycosyl phenylsulfones were converted in high yield into glycals after reductive lithiation with lithium naphthalenide, followed by elimination of the substituent at C-2.