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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

Abstract:

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 st...

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Publication status:
Published

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Publisher copy:
10.1039/p19870001785

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Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
8
Pages:
1785-1791
Publication date:
1987-08-01
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
Source identifiers:
42866
Language:
English
Pubs id:
pubs:42866
UUID:
uuid:cd347711-a895-40e5-b550-7dfad613a155
Local pid:
pubs:42866
Deposit date:
2012-12-19

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