549505-93-3

Upstream product

• 108-24-7 acetic anhydride 
• 389620-75-1 prop-2-ynyl 2,3-dideoxy-6-O-p-toluenesulfonyl-α-D-erythro-hex-2-enopyranoside 
• 188605-67-6 (1-prop-2-ynyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

Synthesis and transformations of new annulated pyranosides using the Pauson-Khand reaction

The synthesis and transformations of new annulated pyranosides are described. These adducts were prepared by Pauson-Khand reaction on differently functionalized prop-2-ynyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosides (1-8). Compound 1 with a free hydroxyl group at C-4 afforded significant amounts of the hydrogenolysis product 12 in addition to the normal adduct 13. The C-4 O-protected similar precursors (2-8) gave PK products in yields ranging from 39 to 63%. Pauson-Khand adduct 19 provided intermediate 23 after selective manipulation. The oxidation plus decarbonylation synthetic sequence applied to intermediate 23 gave a poor yield of compound 24 using Wilkinson's catalyst. The t-butyl hydroperoxide promoted decarbonylation of product 23 afforded formate 25 in a typical Baeyer-Villiger rearrangement. The Ferrier-II reaction on intermediate 45, readily available from compound 9, afforded the hydrindane-type derivative 46 in 34% yield using a Ferrier-II type reaction.