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1.
Org Biomol Chem ; 8(7): 1619-22, 2010 Apr 07.
Artigo em Inglês | MEDLINE | ID: mdl-20237673

RESUMO

A computational investigation on the origin of the stereoselectivity of 6-exo-trig radical cyclization of alpha,beta-unsaturated ester-tethered sugars has revealed that a boat-like transition state, which keeps the ester in a planar conformation, holds the chiral information. Following this model, the stereocenter to which the ester functionality is connected reports the chirality to the newly formed stereocenter via a 1,4-transfer mechanism.


Assuntos
Carboidratos/química , Ciclização , Ésteres/química , Modelos Moleculares , Estereoisomerismo
2.
Carbohydr Res ; 343(3): 536-40, 2008 Feb 25.
Artigo em Inglês | MEDLINE | ID: mdl-18068693

RESUMO

Several novel N-1, N-2, and S-5 tetrazole and 1,3,4-oxadiazole derivatives of alpha,alpha-trehalose disubstituted at C-6,6', with potential synthetic and pharmacological interest were prepared from commercial tetrazoles and 1,3,4-oxadiazoles in reaction with hexa-O-benzyl-6,6'-di-O-triflyl-alpha,alpha-trehalose.


Assuntos
Compostos Heterocíclicos/síntese química , Trealose/síntese química , Oxidiazóis , Tetrazóis
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