piperidines and benzenesulfinic-acid

piperidines has been researched along with benzenesulfinic-acid* in 2 studies

Other Studies

2 other study(ies) available for piperidines and benzenesulfinic-acid

Article	Year
Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-( Journal of the American Chemical Society, 2006, Jun-21, Volume: 128, Issue:24 The synthesis of d- and l-glycero-alpha-manno-thioheptopyranosides, protected with 4,6-O-alkylidene-type acetals is described. In glycosylations carried out with preactivation with the 1-benzenesulfinylpiperidine/trifluoromethanesulfonic anhydride couple, both the D- and L-glycero series exhibit excellent beta-selectivity with a range of glycosyl acceptors. In contrast, a 4,7-O-alkylidene acetal was found not to afford beta-selectivity. With a 4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetal protected thioglycoside, excellent beta-selectivity was obtained in glycosylation reactions, and subsequent treatment with tributyltin hydride and azoisobutyronitrile brought about clean fragmentation to the 6-deoxy-glycero-beta-D-manno-heptopyranosides. This chemistry was applied to the stereocontrolled synthesis of methyl alpha-L-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl-(1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L-rhamno-pyranoside, a component of the lipopolysaccharide from Plesimonas shigelloides. Topics: Acetals; Alkenes; Azo Compounds; Carbohydrate Conformation; Carbohydrate Sequence; Deoxy Sugars; Glycosylation; Heptoses; Lipopolysaccharides; Mesylates; Methylglycosides; Models, Chemical; Molecular Sequence Data; Nitriles; Oligosaccharides; Piperidines; Plesiomonas; Rhamnose; Stereoisomerism; Sulfinic Acids; Trialkyltin Compounds	2006
1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages. Journal of the American Chemical Society, 2001, Sep-19, Volume: 123, Issue:37 The combination of 1-benzenesulfinyl piperidine (BSP) and trifluoromethanesulfonic anhydride (Tf(2)O) forms a new, powerful, metal-free thiophile that can readily activate both armed and disarmed thioglycosides, via glycosyl triflates, in a matter of minutes at -60 degrees C in dichloromethane, in the presence of 2,4,6-tri-tert-butylpyrimidine (TTBP). The glycosyl triflates are rapidly and cleanly converted to glycosides, upon treatment with alcohols, in good yield and selectivity. Topics: Anhydrides; Carbohydrate Sequence; Cold Temperature; Drug Stability; Glycosides; Mesylates; Molecular Sequence Data; Piperidines; Sulfinic Acids; Thioglycosides	2001

Article

Year

Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(

Journal of the American Chemical Society, 2006, Jun-21, Volume: 128, Issue:24

The synthesis of d- and l-glycero-alpha-manno-thioheptopyranosides, protected with 4,6-O-alkylidene-type acetals is described. In glycosylations carried out with preactivation with the 1-benzenesulfinylpiperidine/trifluoromethanesulfonic anhydride couple, both the D- and L-glycero series exhibit excellent beta-selectivity with a range of glycosyl acceptors. In contrast, a 4,7-O-alkylidene acetal was found not to afford beta-selectivity. With a 4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetal protected thioglycoside, excellent beta-selectivity was obtained in glycosylation reactions, and subsequent treatment with tributyltin hydride and azoisobutyronitrile brought about clean fragmentation to the 6-deoxy-glycero-beta-D-manno-heptopyranosides. This chemistry was applied to the stereocontrolled synthesis of methyl alpha-L-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl-(1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L-rhamno-pyranoside, a component of the lipopolysaccharide from Plesimonas shigelloides.

Topics: Acetals; Alkenes; Azo Compounds; Carbohydrate Conformation; Carbohydrate Sequence; Deoxy Sugars; Glycosylation; Heptoses; Lipopolysaccharides; Mesylates; Methylglycosides; Models, Chemical; Molecular Sequence Data; Nitriles; Oligosaccharides; Piperidines; Plesiomonas; Rhamnose; Stereoisomerism; Sulfinic Acids; Trialkyltin Compounds

2006

1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.

Journal of the American Chemical Society, 2001, Sep-19, Volume: 123, Issue:37

The combination of 1-benzenesulfinyl piperidine (BSP) and trifluoromethanesulfonic anhydride (Tf(2)O) forms a new, powerful, metal-free thiophile that can readily activate both armed and disarmed thioglycosides, via glycosyl triflates, in a matter of minutes at -60 degrees C in dichloromethane, in the presence of 2,4,6-tri-tert-butylpyrimidine (TTBP). The glycosyl triflates are rapidly and cleanly converted to glycosides, upon treatment with alcohols, in good yield and selectivity.

Topics: Anhydrides; Carbohydrate Sequence; Cold Temperature; Drug Stability; Glycosides; Mesylates; Molecular Sequence Data; Piperidines; Sulfinic Acids; Thioglycosides

2001