J. Kuszmann, P. Sohår
May 1, 1976
Citations
0
Influential Citations
8
Citations
Journal
Carbohydrate Research
Abstract
Abstract Treatment of 2,4- O -benzylidene-1,6-di- O -tosyl- D -glucitol ( 1 ) with potassium thiolbenzoate afforded the 6- S -benzoyl compound 2 and its 5-benzoate 4 , the structure of which was proved chemically. When 1 was acetylated and then treated with the thiolate, the acetylated 6- S -benzoyl compound 19 was obtained in good yield in addition to some 1,6-di- S -benzoyl derivative 21 . Treatment of 19 with acetic anhydride-acetic acid-sulfuric acid afforded 2,3,4,5-tetra- O -acetyl-6- S -acetyl-1- O -tosyl- D -glucitol ( 26 ), which was converted by sodium methoxide into a mixture of 1,5-anhydro-6-thio- D -glucitol ( 28 ) and 1,6-thioanhydro- D -glucitol ( 29 ). These two compounds were isolated as their acetates ( 30 and 31 ) by column chromatography, or by converting 28 into its S -trityl derivative ( 32 ).