- Preparation of O-, S- and N-benzyl derivatives of 1,6-anhydro-β-D-hexopyranoses via aziridine ring opening
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The aziridine ring opening of N-tosylepimino carbohydrates 1-6 having D-allo, D-manno, D-galacto and D-talo configurations with benzyl alcohol, benzylamine and phenylmethanethiol afforded 2-, 3- and 4-O-benzyl-, benzylsulfanyl and benzylamino derivatives of 1,6-anhydro-β-D-hexopyranoses of D-gluco, D-galacto and D-manno configurations 7-23 in 44-99% yields. Hexenopyranoses 24-26 were prepared from tosylepimino carbohydrates 1, 4 and 5 by intramolecular rearrangement of the aziridine ring.
- Kroutil, Jiri,Karban, Jindrich,Trnka, Tomas,Budesinsky, Milos,Cerny, Miloslav
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p. 1805 - 1819
(2007/10/03)
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- Synthesis and NMR spectra of 1,6-anhydro-2,3-dideoxy-2,3-epimino- and 1,6-anhydro-3,4-dideoxy-3,4-epimino-β-D-hexopyranoses
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A complete series of 2,3-dideoxy-2,3-epimino-and 3,4-dideoxy-3,4-epimino-1,6-anhydro-β-D-hexopyranoses were prepared by lithium aluminum hydride reduction of the corresponding trans-azido tosylates or trans-azido epoxides of 1,6-anhydro-β-D-hexopyranoses. The structure of the epimino derivatives was confirmed by 1H and 13C NMR spectra.
- Karban, Jindrich,Budesinsky, Milos,Cerny, Miloslav,Trnka, Tomas
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p. 799 - 819
(2007/10/03)
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