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Citation: SHE Ji. Highly Selective p-Monotosylation of Hydroxyls of Saccharide in the Presence of Ag₂O[J]. Chinese Journal of Applied Chemistry, ;2005, 22(2): 230-232. shu

Highly Selective p-Monotosylation of Hydroxyls of Saccharide in the Presence of Ag₂O

SHE Ji ^,

1.
Department of Chemistry, Guangdong Medical College, Zhanjiang 524023

Corresponding author: SHE Ji,
Received Date: 19 March 2004
Available Online: 26 July 2004

Silver(Ⅰ) oxide was applied to the selective p-tosylation of hydroxyls of saccharide. The reaction of p-methylphenyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside(A) with a stoichiometric amount of p-toluenesulfonyl chloride(TsCl) in the presence of silver(Ⅰ) oxide and a catalytic amount of potassium iodide selectively led to the monotosylate derivative:p-methylphenyl 3-O-p-toluenesulfonyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside(B) in a high yield(97%). A possible mechanism of the reaction is proposed. The rational reaction process is that at n(TsCl):n(Ag₂O):n(A):n(KI)=1.2:1.5:1.0:0.2, the mixture is stirred at room temperature for 8 h, 2.74 g(97%)B could be isolated from 2.0 g of compound A.
- silver(Ⅰ) oxide,
- selective p-tosylation,
- saccharide hydroxyl
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Highly Selective p-Monotosylation of Hydroxyls of Saccharide in the Presence of Ag₂O