Hydrogenolysis of carbohydrate acetals, ketals, and cyclic orthoesters with lithium aluminium hydride – aluminium trichloride

DOI Web Site 被引用文献8件

書誌事項

公開日
1969-04-01
権利情報
  • http://www.nrcresearchpress.com/page/about/CorporateTextAndDataMining
DOI
  • 10.1139/v69-194
公開者
Canadian Science Publishing

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説明

<jats:p> The reduction of hexofuranose and hexopyranose acetals with LiAlH<jats:sub>4</jats:sub>–AlCl<jats:sub>3</jats:sub> (1:1, probably AlH<jats:sub>2</jats:sub>Cl) to the corresponding ethers proceeds in similar fashion as that of simple acetals and ketals (Scheme I) (refs. 1–7). Certain O-methyl and O-benzyl derivatives, not readily obtainable otherwise, are conveniently synthesized from appropriate acetals in this way. Cyclic orthoesters of glucofuranose may be selectively reduced to acetals; the steric course of such reduction has been shown unequivocally in the case of orthoformates (Scheme II). Of several cleavable groups, the ease of hydrogenolysis is (a) cyclic orthoester > isopropylidene ketal, cyclohexylidene ketal > benzylidene acetal > ethylidene acetal > formal and (b) 5,6-O-linked or 3,5-O-linked acetal or ketal > 1,2-O-linked acetal or ketal. </jats:p>

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