Intramolecular cyclization of pentose and hexose dithioacetals
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Add time:07/24/2019 Source:sciencedirect.com
The intramolecular cyclization of O-tosyl derivatives of dithioacetals of d-ribose, d-arabinose, and d-glucose was investigated. p-Toluenesulfonylation of d-glucose diethyl dithioacetal gave 3,6-anhydro-d-glucose diethyl dithioacetal. Variously substituted 5-O-tosyl-d-glucose dibenzyl dithioacetals gave derivatives of either 2,5-anhydro-l-idose dibenzyl dithioacetal, benzyl 1,5-dithio-l-idopyranoside, or l-idose dibenzyl dithioacetal. Likewise, 4-O-tosyl-d-glucose dibenzyl dithioacetal derivatives gave benzyl 1,4-dithio-d-galactofuranoside derivatives.
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