Preparation of O-, S- and N-Benzyl Derivatives of 1,6-Anhydro-beta-D-Hexopyranoses via Aziridine Ring Opening

0166676 - UCHP-M 20020373 RIV CZ eng J - Journal Article
Kroutil, J. - Karban, Jindřich - Trnka, T. - Buděšínský, Miloš - Černý, M.
Preparation of O-, S- and N-Benzyl Derivatives of 1,6-Anhydro-beta-D-Hexopyranoses via Aziridine Ring Opening.
Collection of Czechoslovak Chemical Communications. Roč. 67, č. 12 (2002), s. 1805-1819. ISSN 0010-0765
R&D Projects: GA ČR GA203/01/0862
Institutional research plan: CEZ:MSM 113100001
Keywords : carbohydrates * stereospecific synthesis * NMR spectroscopy
Subject RIV: CC - Organic Chemistry
Impact factor: 0.848, year: 2002

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-b-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. .
Permanent Link: http://hdl.handle.net/11104/0063791