Catalytic and Regioselective Functionalization of Carbohydrates via Mitsunobu Reaction

2014 Fiscal Year Final Research Report

• Project/Area Number: 24790014
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Chemical pharmacy
• Research Institution: Nagasaki University
• Principal Investigator: MURAMATSU Wataru 長崎大学, 医歯薬学総合研究科(薬学系), 助教 (60578714)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: 糖官能基化

Outline of Final Research Achievements

The catalytic regioselective Mitsunobu reaction of nonprotected carbohydrates using organotin dichloride has been examined. Unfortunately, this attempt has not been achieved so far.
The catalytic regioselective monosulfonylation of nonprotected carbohydrates using organotin dichloride under mild conditions has been developed. The regioselectivity of the sulfonylation is attributed to the intrinsic character of the carbohydrates derived from the relative stereochemistry between their hydroxy groups.
A catalytic process for the chemo- and regioselective functionalization of nonprotected carbohydrates has been developed. This novel process allows selective thiocarbonylation, acylation, and sulfonylation of a particular hydroxy group in a particular carbohydrate in the simultaneous presence of structurally similar carbohydrates such as anomers. In addition, the chemoselectivity can be switched by regulating only the length of the alkyl chain in the organotin catalyst.

Free Research Field

有機合成化学