SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINET
A general approach to the synthesis of polyfunctionalised amino acids from sugar lactones, in which nucleophilic displacement by azide ion of O-trifluoromethanesulphonyl esters adjacent to the lactone carbonyl is the key step, is discussed and is exemplified by the synthesis of the D-amino acid (2R,...
| Main Authors: | , , , , , |
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| Format: | Journal article |
| Language: | English |
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1987
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| _version_ | 1826297181564305408 |
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| author | Baird, P Dho, J Fleet, G Peach, J Prout, K Smith, P |
| author_facet | Baird, P Dho, J Fleet, G Peach, J Prout, K Smith, P |
| author_sort | Baird, P |
| collection | OXFORD |
| description | A general approach to the synthesis of polyfunctionalised amino acids from sugar lactones, in which nucleophilic displacement by azide ion of O-trifluoromethanesulphonyl esters adjacent to the lactone carbonyl is the key step, is discussed and is exemplified by the synthesis of the D-amino acid (2R,3S,4R)-3,4-dihydroxyproline from D-ribonolactone; unexpectedly, displacement of a triflate by azide in the C-2 position of ribonolactone occurs with retention of configuration. The X-ray crystal structures of 2-azido-3,4-O-(R)- benzylidene-2-deoxy-D-ribono-1,5-lactone, 2-azido-2-deoxy-D-ribono-1,4-lactone, and (2R,3S,4R)-3,4-dihydroxyproline are reported. l.r. spectroscopy does not discriminate reliably between 1,4-and 1,5-lactones, and X-ray crystallography is necessary to provide reliable structural information in this area. |
| first_indexed | 2024-03-07T04:27:39Z |
| format | Journal article |
| id | oxford-uuid:cd347711-a895-40e5-b550-7dfad613a155 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T04:27:39Z |
| publishDate | 1987 |
| record_format | dspace |
| spelling | oxford-uuid:cd347711-a895-40e5-b550-7dfad613a1552022-03-27T07:27:06ZSYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINETJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:cd347711-a895-40e5-b550-7dfad613a155EnglishSymplectic Elements at Oxford1987Baird, PDho, JFleet, GPeach, JProut, KSmith, PA general approach to the synthesis of polyfunctionalised amino acids from sugar lactones, in which nucleophilic displacement by azide ion of O-trifluoromethanesulphonyl esters adjacent to the lactone carbonyl is the key step, is discussed and is exemplified by the synthesis of the D-amino acid (2R,3S,4R)-3,4-dihydroxyproline from D-ribonolactone; unexpectedly, displacement of a triflate by azide in the C-2 position of ribonolactone occurs with retention of configuration. The X-ray crystal structures of 2-azido-3,4-O-(R)- benzylidene-2-deoxy-D-ribono-1,5-lactone, 2-azido-2-deoxy-D-ribono-1,4-lactone, and (2R,3S,4R)-3,4-dihydroxyproline are reported. l.r. spectroscopy does not discriminate reliably between 1,4-and 1,5-lactones, and X-ray crystallography is necessary to provide reliable structural information in this area. |
| spellingShingle | Baird, P Dho, J Fleet, G Peach, J Prout, K Smith, P SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINET |
| title | SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINET |
| title_full | SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINET |
| title_fullStr | SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINET |
| title_full_unstemmed | SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINET |
| title_short | SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINET |
| title_sort | synthesis of 2r 3s 4r 3 4 dihydroxyproline from d ribonolactone an approach to the synthesis of polyfunctionalized d amino acids from sugar lactones x ray molecular structures of 2 azido 3 4 o r benzylidene 2 deoxy d ribono 1 5 lactone 2 azido 2 deoxy d ribono 1 4 lactone and 2r 3s 3r 3 4 dihydroxyprolinet |
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