Chemistry 251 Laboratory -- Spring 2001
Coniferin Project Home Page

Index

• 2000 Coniferin Project Home Page
• Students working on this project
• Table of Reagents and Amounts Available
• Notes on preparation of acetobromoglucose

Daubresse, N., R.; Francesch, C.; Mhamdi, F.; Rolando, C. Synthesis, 1998, 157-161.

Coniferin is an important metabolite in conifers, serving as an important intermediate in cell wall lignification, as well as having other biological roles. Last year a French group reported an elagent synthesis of this compound starting from vanillin. In a one-pot reaction, the vanillin is first glucosylated on the phenolic hydroxyl and then a Wittig reaction is used to introduce the double bond. After unmasking the aldehyde, and reduction to the alcohol, the acetates are removed with methoxide to afford the desired coniferin. (Note: It will be necessary to first prepare acetobromoglucose from glucose pentaacetate.)

The table below lists the chemicals that we will have available for this project. If you need something that is not on this list, consult with the mentor for your project. Also note the "Amount/group" column. This is the total amount of material available for each group to use on the project.

Reagent	Source	Amount/group	Location	Comments
Beta-D-Glucose pentaacetate	Aldrich Cat. # G235-4	15 g	TA room
Hydrogen Bromide 30 wt% solution in acetic acid	Aldrich Cat. # 24,863-0	25 mL	TA room
Vanillin	Aldrich Cat. # V110-4	15 mL	TA Room
(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide	Aldrich Cat. # 22,385-9	2 g	TA Room
Tris[2-(2-methoxyethoxy)ethyl]amine TDA-1	Aldrich Cat # 30,124-8	10 g	TA Room