Organotin‐Catalyzed Highly Regioselective Thiocarbonylation of Nonprotected Carbohydrates and Synthesis of Deoxy Carbohydrates in a Minimum Number of Steps

Nonprotected carbohydrates: The catalytic regioselective thiocarbonylation of carbohydrates by using organotin dichloride under mild conditions was demonstrated. The reaction afforded various deoxy saccharides in high yields and excellent regioselectivity in a minimum number of steps. The regioselectivity of the thiocarbonylation is attributed to the intrinsic character of the carbohydrates based on the stereorelationship of their hydroxy groups (see scheme).