Chemistry
Trimethylsilylation of Sugars via Hexamethyldisilazane
Document Type
Poster Presentation
Location
Indianapolis, IN
Subject Area
Chemistry
Start Date
11-4-2014 8:30 AM
End Date
11-4-2014 9:30 AM
Sponsor
Harold Pinnick (Purdue University Calumet)
Description
To this date, no techniques have been determined to make physically large amounts of the products described herein. This experiment will serve as an extension to the previous study done by Harold W. Pinnick and Nordin H. Lajis on N-bromosuccinimide oxidation of silyl ethers. It is also a further extension on research currently being conducted at Purdue University Calumet. It is known that trimethylsilyl is a very good protecting agent for hydroxyl groups. In order to get rid of hydrogen bonding, we must make pertrimethysilyl derivatives, which increases volatility. We must also volatize the compound in order to get it into GC/MS. Hopefully, this strategy can be used with compounds where you might get a cyclic ester. Attractive compounds for those substrates are carbohydrates which are readily available and would be very good to show selectivity because of the large number of hydroxyl groups.
The challenge we face is being able to selectively oxidize substrates. Along with determining selectivity, we also want to be able to use these methods to determine a way to generate physically large amounts (preferably 1-10 grams) of these compounds so that they can be used synthetically. Although one only needs very small amounts for GC/MS, we want to determine a way to scale it up to a larger amount by optimizing the persilation of carbohydrates so that this methodology can be used by others.
A standard procedure has been developed that gave us pure results for a small scale reaction during the Fall semester of 2013. The next steps are to generate a large scale reaction with glucose that can be used as a standard. Once this has been completed, standards for the remaining sugars will be generated.
Trimethylsilylation of Sugars via Hexamethyldisilazane
Indianapolis, IN
To this date, no techniques have been determined to make physically large amounts of the products described herein. This experiment will serve as an extension to the previous study done by Harold W. Pinnick and Nordin H. Lajis on N-bromosuccinimide oxidation of silyl ethers. It is also a further extension on research currently being conducted at Purdue University Calumet. It is known that trimethylsilyl is a very good protecting agent for hydroxyl groups. In order to get rid of hydrogen bonding, we must make pertrimethysilyl derivatives, which increases volatility. We must also volatize the compound in order to get it into GC/MS. Hopefully, this strategy can be used with compounds where you might get a cyclic ester. Attractive compounds for those substrates are carbohydrates which are readily available and would be very good to show selectivity because of the large number of hydroxyl groups.
The challenge we face is being able to selectively oxidize substrates. Along with determining selectivity, we also want to be able to use these methods to determine a way to generate physically large amounts (preferably 1-10 grams) of these compounds so that they can be used synthetically. Although one only needs very small amounts for GC/MS, we want to determine a way to scale it up to a larger amount by optimizing the persilation of carbohydrates so that this methodology can be used by others.
A standard procedure has been developed that gave us pure results for a small scale reaction during the Fall semester of 2013. The next steps are to generate a large scale reaction with glucose that can be used as a standard. Once this has been completed, standards for the remaining sugars will be generated.