Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone
Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (12)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (1) and L-glutamic acid (6) as chiral templates. The key step in the first appr...
Guardado en:
| Publicado: |
2000
|
|---|---|
| Materias: | |
| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v11_n3_p765_Zunszain http://hdl.handle.net/20.500.12110/paper_09574166_v11_n3_p765_Zunszain |
| Aporte de: |
| id |
paper:paper_09574166_v11_n3_p765_Zunszain |
|---|---|
| record_format |
dspace |
| spelling |
paper:paper_09574166_v11_n3_p765_Zunszain2023-06-08T15:56:27Z Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone lactone derivative thiolactone article drug synthesis enantiomer priority journal stereospecificity Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (12)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (1) and L-glutamic acid (6) as chiral templates. The key step in the first approach was the SmI2-promoted 2,3-deoxygenation of a 4-thio-L-lyxono-1,4-lactone derivative, prepared from 1. The other strategy, which starts from 6, involves the (5S)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (8) as chiral precursor. This was converted into a 4,5-thiirane derivative via the corresponding 4,5-epoxide. Regioselective opening of the thiirane ring by acetate followed by O-deacetylation gave 12 (40% overall yield from 8). Copyright (C) 2000 Elsevier Science Ltd. 2000 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v11_n3_p765_Zunszain http://hdl.handle.net/20.500.12110/paper_09574166_v11_n3_p765_Zunszain |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
lactone derivative thiolactone article drug synthesis enantiomer priority journal stereospecificity |
| spellingShingle |
lactone derivative thiolactone article drug synthesis enantiomer priority journal stereospecificity Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| topic_facet |
lactone derivative thiolactone article drug synthesis enantiomer priority journal stereospecificity |
| description |
Enantiomerically pure (4R)-4-hydroxymethyl-4-thiobutyro-1,4-lactone [(5R)-dihydro-5-(hydroxymethyl)-2(3H)-thiophenone (12)] and derivatives were synthesized by two enantiospecific sequences employing D-ribono-1,4-lactone (1) and L-glutamic acid (6) as chiral templates. The key step in the first approach was the SmI2-promoted 2,3-deoxygenation of a 4-thio-L-lyxono-1,4-lactone derivative, prepared from 1. The other strategy, which starts from 6, involves the (5S)-dihydro-5-(p-tolylsulfonyloxymethyl)-2-(3H)-furanone (8) as chiral precursor. This was converted into a 4,5-thiirane derivative via the corresponding 4,5-epoxide. Regioselective opening of the thiirane ring by acetate followed by O-deacetylation gave 12 (40% overall yield from 8). Copyright (C) 2000 Elsevier Science Ltd. |
| title |
Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| title_short |
Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| title_full |
Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| title_fullStr |
Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| title_full_unstemmed |
Two approaches to the enantioselective synthesis of (4R)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| title_sort |
two approaches to the enantioselective synthesis of (4r)-(-)-4-hydroxymethyl-4-thiobutyro-1,4-lactone |
| publishDate |
2000 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v11_n3_p765_Zunszain http://hdl.handle.net/20.500.12110/paper_09574166_v11_n3_p765_Zunszain |
| _version_ |
1768544648494579712 |