Carbohydrate Research 2015-11-19

Reductive opening of carbohydrate phenylsulfonylethylidene (PSE) acetals.

Florence Chéry, Elena Cabianca, Arnaud Tatibouët, Ottorino De Lucchi, Thisbe K Lindhorst, Patrick Rollin

Index: Carbohydr. Res. 417 , 117-24, (2015)

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Abstract

The phenylsulfonylethylidene (PSE) acetal is a relatively new protecting group in carbohydrate chemistry. However, carbohydrate-derived phenylsulfonylethylidene (PSE) acetals show a different behavior in reductive desulfonylation than simple symmetrical acetals. Here we have investigated various SET-type reaction conditions in order to open PSE acetals regioselectively and to produce chiral ω-hydroxyethenyl ethers. Whereas sodium amalgam leads to a mixture of regioisomeric vinyl ethers besides the ethylidene acetal, samarium iodide is suited for regioselective ring opening. This is shown with seven different carbohydrate PSE acetals, both of the 1,3-dioxane and the 1,3-dioxolane type. Copyright © 2015 Elsevier Ltd. All rights reserved.