Formation of Ethers and Esters Except Sulfonates

5- tri-181 and 3,4,5,6-tetra-O-benzoyl122 182 (27) derivatives are formed by reaction with controlled proportions of benzoyl chloride an analogous conversion of D-galactose diethyl dithioacetal into its 

6- tribenzoate was reporte4 to occur under Schotten-Baumann conditions.183 A tetra-O-acetyl-D-glucose dithioacetal (93) has been directly prepared from the parent dithioacetal,184 and found to be identical to, or readily interconvertible into, products obtained by detritylation of 2,3,4,5-tetra-0-acetyl-6-0-trityl-D-glucose diethyl dithioacetal and by controlled mercaptolysis of 2,3,4,6-tetra-O- 

Other derivatives of hydroxyl groups, shown to form without apparent complications, include phenylurethans,202 mixed203 and cyclic204 carbonates, diphenylphosphoric205 esters, and terminal 1-adamantoates206 cyclic sulfites204 are produced by the action of thionyl chloride. 

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