
pmid: 14894346
Publisher Summary This chapter discusses methyl ethers of D -galactose. The 2,3,4,6-tetramethyl- D -galactopyranos is obtained by the full methylation of the methyl α- or β- D -galactopyranosides, followed by acid hydrolysis of the products. Selective trimethylation at positions 3, 4, and 6 has been accomplished by starting with the 1,2-isopropylidene- D -galactopyranose. The supposed 1,3-anhydro- D -galactopyranoset, the structure of which is assigned from the fact that it is not oxidized by periodate, would have supplied a starting material for 2,4,6-trimethyl- D -galactose, but subsequent investigation as shown that its full methylation and the subsequent hydrolysis of the product yields 2,3,5-trimethyl- D -galactose , proving that this galactosan is actually l,6-anhydro-α-D-galactofuranose. Sugar is obtained in crystalline form by methylation of methyl 3,4-isopropylidene-β- D -galactopyranosid 6-nitrate, followed by stepwise removal of the substituent radicals. The synthesis of the sugar presented certain technical problems. While the obvious starting material is either of the methyl 4,6-benzylidene- D -galactopyranosides it is quite clear that neither carboxylic nor sulphonic nor nitric esters could be used for temporary masking of hydroxyls 2 and 3.
Methyl Ethers, Galactose
Methyl Ethers, Galactose
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