Hexahydro-Pyrrolo[1',2',5':3,4,5]Thiazolo[3,4-c]Oxazol-1-ones: New Chiral Tricyclic L-Cysteine and D-Penicillamine Derivatives

Teresa M.V.D. Pinho e Melo; Susana M.M. Lopes; Antonio M. d'A. Rocha Gonsalves; Agnieszka Kaczor; Rui Fausto; Jose A. Paixao; Ana Matos Beja; Manuela Ramos Silva

doi:10.2174/157017806779116996

ISSN: 1570-1786
E-ISSN: 1875-6255

Hexahydro-Pyrrolo[1',2',5':3,4,5]Thiazolo[3,4-c]Oxazol-1-ones: New Chiral Tricyclic L-Cysteine and D-Penicillamine Derivatives
Authors: Teresa M.V.D. Pinho e Melo¹, Susana M.M. Lopes², Antonio M. d'A. Rocha Gonsalves³, Agnieszka Kaczor⁴, Rui Fausto⁵, Jose A. Paixao⁶, Ana Matos Beja⁷ and Manuela Ramos Silva⁸
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¹ Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal. ² Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal. ³ Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal. ⁴ Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal. ⁵ Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal. ⁶ Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal. ⁷ Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal. ⁸ Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal.
Source: Letters in Organic Chemistry, Volume 3, Issue 11, Nov 2006, p. 820 - 826
DOI: https://doi.org/10.2174/157017806779116996
- Available online: 01 Nov 2006

Abstract

A simple and efficient approach to the synthesis of the new chiral hexahydropyrrolo [1',2',5':3,4,5]thiazolo[3,4-c]oxazol-1-one ring system is reported. Infrared spectroscopy, quantum-chemical calculations and X-ray analysis allowed the stereochemistry assignment of (2aS,4aR,6aR)-2a,3,4,4a,6,6ahexahydropyrrolo-[ 1',2',5':3,4,5]thiazolo[3,4-c]oxazol-1-one.

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2006-11-01

2025-09-17

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Article Type: Research Article

Keyword(s): DFT(B3LYP)/6-311++G(d,p) calculations; Hexahydro-pyrrolo[1',2',5':3,4,5]thiazolo[3,4-c]oxazol-1-ones; Infrared spectroscopy; L-Cysteine and D-Penicillamine derivatives; Matrix isolation

Hexahydro-Pyrrolo[1',2',5':3,4,5]Thiazolo[3,4-c]Oxazol-1-ones: New Chiral Tricyclic L-Cysteine and D-Penicillamine Derivatives

Abstract

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