Glucose methyl ethers

Glucose methyl-ether oxide Fig. 3.13. Methyl D-glucopyranoside formation mechanism... 

MeSSiMe3 or PhSSiMe3, Znl2, Bu4N I. In this case the 6-O-methyl ether was cleaved selectively from permethylated glucose. 

A study of the reductive cleavage of a series of alkoxymethyl ethers using the glucose backbone shows that, depending on the reagent, excellent selectivity can be obtained for deprotection vs. methyl ether formation for most of the common protective groups. ... 

Boeseken, J., The Use of Boric Acid for the Determination of the Configuration of Carbohydrates, IV, 189-210 Bonner, William A., Friedel-Crafts and Grignard Processes in the Carbohydrate Series, VI, 251-289 Bourne, E. J., and Peat, Stanley, The Methyl Ethers of D-Glucose, V, 145-190 Bourne, E. J. See also, Barker, S. A. 

In this article, the authors have endeavored to summarize the methods of synthesis and the proofs of constitution of all the known methyl ethers of D-glucopyranose and D-glucofuranose. Acyclic glucose ethers are not considered in this review. Later articles will deal with monosaccharides other than glucose. It has not been possible to discuss in full all the reactions involved, but to offset this disadvantage the bibliography has been made as complete as possible and tables have been compiled of the physical properties of the methyl-D-glucoses and of their more important derivatives. 

The naturally-occurring 1,6-linked glucose polymers furnish other sources of 2,3,4-trimethyl-D-glucose, which has been isolated from the hydrolysis products of the methyl ethers of gentiobiose,112 118 melibiose,114 raffmose106 116 and dextran.78 74,116... 

This particular trimethylglucose is unique in that it was separated in crystalline form from the hydrolyzates of the methyl ethers of several naturally-occurring glucose polymers almost two decades before it was synthesized from glucose. These natural sources, which still furnish the most convenient routes for the preparation of 2,3,6-trimethyl-D-glucose, include maltose,124-128 cellobiose,127,128 lactose,122-181 starch,71,182 glycogen,188,184 cellulose,185-187 and lichenin. 188,189 The literature pub-... 

Tetramethyl-D-glucose is frequently isolated after hydrolysis of the methyl ethers of naturally-occurring glucose polymers (e.g. maltose,... 

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