110522-37-7Relevant academic research and scientific papers
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.
Stereoselective synthesis of 2-deoxy-β-glycosides from glycal precursors. 1. Stereochemistry of the reactions of D-glucal derivatives with phenylsulfenyl chloride and phenylselenenyl chloride
Roush, William R.,Sebesta, David P.,Bennett, Chad E.
, p. 8825 - 8836 (2007/10/03)
The stereoselectivity of the reactions of D-glucal derivatives with PhSCl and PhSeCl is dependent on the presence of an electronegative heteroatom substituent at C(6) and the nature of the functionality at C(4). The C(6)-substituent influences the conformational preferences of the D- glucal derivatives, and greatest stereoselectivity is obtained with those glycals that preferentially exist in the inverted 5H4 half-chair conformation 28b. A polar substituent at C(4) increases the selectivity by stabilizing the episulfonium/episelenonium ion intermediates 31b and 33.
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.
