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Solvent effects in the nucleophilic substitutions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate: trichloroethylene as solvent for stereoselective C- and O-glycosylations.

Kendale JC, Valentín EM, Woerpel KA - Org. Lett. (2014)

Bottom Line: The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent.Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products.Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, New York University , New York, New York 10003, United States.

ABSTRACT
The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products. Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions.

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NucleophilicSubstitution of 2-Deoxyglucopyranosyl Phosphite 11 andEthanol
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Solvent effects in the nucleophilic substitutions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate: trichloroethylene as solvent for stereoselective C- and O-glycosylations.

Kendale JC, Valentín EM, Woerpel KA - Org. Lett. (2014)

NucleophilicSubstitution of 2-Deoxyglucopyranosyl Phosphite 11 andEthanol
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4334250&req=5

sch7: NucleophilicSubstitution of 2-Deoxyglucopyranosyl Phosphite 11 andEthanol
Bottom Line: The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent.Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products.Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, New York University , New York, New York 10003, United States.

ABSTRACT
The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products. Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions.

Show MeSH