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Abstract:

Reaction of 2,3,4,6-tetra-O-acetyl-1,5-anhydro-d-arabino-hex-1-enitol (1; 2-hydroxyglucal tetraacetate) with 1.0-1.5 mol of primary secondary, or tertiary alcohols, in the presence of 0.1-1.0 mol of N-iodosuccinimide (NIS) in acetonitrile as solvent, afforded the α anomers of alkyl 3-deoxyhex-2-enopyranosides in very good yields. The reaction proceeded more slowly, and with poorer yields, in the case of the tetrabenzoate corresponding to 1. When 1 was treated with higher concentrations of 2-propanol, increasing proportions of a reaction by-product, 2-propyl 6-O-acetyl-3,4-dideoxy-α-d-glycero-hex-3-enopyranosid-2-ulose (10), were produced. Such sugar enones as 10 were more readily formed when the starting 2-hydroxyglycal acetate had the lyxo configuration. Thus, two cholesteryl α-hex-3-enopyranosid-2-ulose derivatives were each prepared in one step and with good yields. Remarkable stereoselectivity for the formation of the α anomers was observed in all of these reactions. © 1987.

Registro:

Documento: Artículo
Título:The reaction of 2-hydroxyglycal esters with alcohols in the presence of N-iodosuccinimide, stereoselective synthesis of α anomers of alkyl 3-deoxyhex-2-enopyranosides and 3,4-dideoxyhex-3-enopyranosid-2-uloses
Autor:Varela, O.; de Fina, G.M.; de Lederkremer, R.M.
Filiación:Departamento de Química Orgánica Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
Año:1987
Volumen:167
Número:C
Página de inicio:187
Página de fin:196
DOI: http://dx.doi.org/10.1016/0008-6215(87)80278-1
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v167_nC_p187_Varela

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Citas:

---------- APA ----------
Varela, O., de Fina, G.M. & de Lederkremer, R.M. (1987) . The reaction of 2-hydroxyglycal esters with alcohols in the presence of N-iodosuccinimide, stereoselective synthesis of α anomers of alkyl 3-deoxyhex-2-enopyranosides and 3,4-dideoxyhex-3-enopyranosid-2-uloses. Carbohydrate Research, 167(C), 187-196.
http://dx.doi.org/10.1016/0008-6215(87)80278-1
---------- CHICAGO ----------
Varela, O., de Fina, G.M., de Lederkremer, R.M. "The reaction of 2-hydroxyglycal esters with alcohols in the presence of N-iodosuccinimide, stereoselective synthesis of α anomers of alkyl 3-deoxyhex-2-enopyranosides and 3,4-dideoxyhex-3-enopyranosid-2-uloses" . Carbohydrate Research 167, no. C (1987) : 187-196.
http://dx.doi.org/10.1016/0008-6215(87)80278-1
---------- MLA ----------
Varela, O., de Fina, G.M., de Lederkremer, R.M. "The reaction of 2-hydroxyglycal esters with alcohols in the presence of N-iodosuccinimide, stereoselective synthesis of α anomers of alkyl 3-deoxyhex-2-enopyranosides and 3,4-dideoxyhex-3-enopyranosid-2-uloses" . Carbohydrate Research, vol. 167, no. C, 1987, pp. 187-196.
http://dx.doi.org/10.1016/0008-6215(87)80278-1
---------- VANCOUVER ----------
Varela, O., de Fina, G.M., de Lederkremer, R.M. The reaction of 2-hydroxyglycal esters with alcohols in the presence of N-iodosuccinimide, stereoselective synthesis of α anomers of alkyl 3-deoxyhex-2-enopyranosides and 3,4-dideoxyhex-3-enopyranosid-2-uloses. Carbohydr. Res. 1987;167(C):187-196.
http://dx.doi.org/10.1016/0008-6215(87)80278-1