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Paper | Regular issue | Vol 34, No. 11, 1992, pp.2131-2136
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6150
C-Nucleosides. 20. Ring Transformation of 5-Hydroxy-5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)furan-2(5H)-one with 2-Aminothiophenol and 2-Aminoethanethiol to 1,5-Benzothiazepine and 1,4-Thiazine

Yasutaka Ito, Masakazu Wakimura, Chihiro Ito, and Isamu Maeba*

*Faculty of Pharmacy, Meijo University, Tempaku-ku, Nagoya 468, Japan

Abstract

Treatment of 1 with 2-aminothiophenol afforded 2-[1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)carbonyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (2). Dehydrogenation of 2 with 2,3-dichloro-5,6-dicyano-p-benzoquinone and a trace amount of p-toluenesulfonic acid in benzene afforded 2-[1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)carbonyl]-1,5-benzothiazepin-4(5H)-one (3). The removal of the sugar protecting groups in 3 afforded 2-[1-(1,4-anhydro-2-deoxy-D-erythro-pent-1-enofuranosyl)carbonyl]-1,5-benzothiazepin-4(5H)-one (4) resulting from the abstruction by base of H-1’. Compound (1) was treated with 2-aminoethanethiol to give 3-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-5,6-dihydro-4H-1,4-thiazine-2-carboxaldehyde (5). Deprotection of the compound (5) with aqueous sodium carbonate afforded the deprotected compound (6).