Department
Chemistry and Biochemistry
Faculty Advisor
Stanislaw Wnuk
Location
GC Ballrooms
Start Date
30-3-2016 2:00 PM
End Date
30-3-2016 3:00 PM
Session
Session 3
Session Topic
Poster
Abstract
Reduction reactions are an important area of study in organic synthesis and are used to synthesize a variety of compounds. In particular, the reduction of lactones to their respective lactols or hemiacetals is important for the synthesis of biologically active modified carbohydrates which are often used in drug design. The reduction of the sugar-based lactones to their respective lactols with lithium triethyl borohydride (LiEt3BH) will be the focus of this project. The efficiency of this reagent to reduce sugar lactones to sugar hemiacetals (lactols) will be studied under different reaction parameters to develop an efficient protocol for its uses. The parameters will include temperature, solvent, time and amount of reducing agent for the reductions using the LiEt3BH. The lactones that will be used in this project are D(-)-gulonic acid γ-lactone, D-(+)-ribonic γ-lactone, and delta-gluconolactone. These lactones will then be modified by introducing protecting groups at their free hydroxyl sites. The protecting groups that will be used in this project are isopropylidene, benzoyl, benzyl, acetyl, trityl, and silyl based (TMS and TBDMS). (download pdf for full abstract)
File Type
Poster
Reduction of Sugar Lactones to Lactols with Super-Hydride
GC Ballrooms
Reduction reactions are an important area of study in organic synthesis and are used to synthesize a variety of compounds. In particular, the reduction of lactones to their respective lactols or hemiacetals is important for the synthesis of biologically active modified carbohydrates which are often used in drug design. The reduction of the sugar-based lactones to their respective lactols with lithium triethyl borohydride (LiEt3BH) will be the focus of this project. The efficiency of this reagent to reduce sugar lactones to sugar hemiacetals (lactols) will be studied under different reaction parameters to develop an efficient protocol for its uses. The parameters will include temperature, solvent, time and amount of reducing agent for the reductions using the LiEt3BH. The lactones that will be used in this project are D(-)-gulonic acid γ-lactone, D-(+)-ribonic γ-lactone, and delta-gluconolactone. These lactones will then be modified by introducing protecting groups at their free hydroxyl sites. The protecting groups that will be used in this project are isopropylidene, benzoyl, benzyl, acetyl, trityl, and silyl based (TMS and TBDMS). (download pdf for full abstract)
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Comments
**Abstract Only**