Abstract:
The synthesis of pyranoid and furanoid derivatives of 6-deoxy-4-thio-D-galactose from methyl α-D-glucopyranoside (1) is described. A key intermediate for the synthesis, methyl 2,3-di-O-benzoyl-6-deoxy-4-thio-α-D-galactopyranoside (15) was prepared by different approaches from 1. Regioselectivity for the protection or modification of the hydroxyl groups of 1 or its derivatives was achieved by employing various reagents. The thiol group at C-4 was introduced by nucleophilic substitution of a tosylate by thiocyanate followed by reduction or alkaline methanolysis of the thiocyano group. A by-product of the latter reaction was characterized as a monothiolcarbonate derivative (17), whose conformation was studied by molecular mechanics calculations. Acetolysis of methyl 6-deoxy-4-thio-α-D-galactopyranoside (16) afforded ring sulfur containing derivatives of 6-deoxy-4-thio-D-galactofuranose, which are described for the first time. © 1990.
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Citas:
---------- APA ----------
Cicero, D., Varela, O. & De Lederkremer, R.M.
(1990)
. Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose. Tetrahedron, 46(4), 1131-1144.
http://dx.doi.org/10.1016/S0040-4020(01)86679-5---------- CHICAGO ----------
Cicero, D., Varela, O., De Lederkremer, R.M.
"Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose"
. Tetrahedron 46, no. 4
(1990) : 1131-1144.
http://dx.doi.org/10.1016/S0040-4020(01)86679-5---------- MLA ----------
Cicero, D., Varela, O., De Lederkremer, R.M.
"Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose"
. Tetrahedron, vol. 46, no. 4, 1990, pp. 1131-1144.
http://dx.doi.org/10.1016/S0040-4020(01)86679-5---------- VANCOUVER ----------
Cicero, D., Varela, O., De Lederkremer, R.M. Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose. Tetrahedron. 1990;46(4):1131-1144.
http://dx.doi.org/10.1016/S0040-4020(01)86679-5