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The use of the acetonide derivative in the preparation of D‐ threo ‐chloramphenicol‐1‐ 3 H and its nitroso derivative
Author(s) -
Heys J. Richard
Publication year - 1981
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580181206
Subject(s) - chloramphenicol , chemistry , epimer , acetonide , ketone , derivative (finance) , stereochemistry , organic chemistry , antibiotics , biochemistry , triamcinolone acetonide , medicine , surgery , financial economics , economics
An efficient synthesis of millimolar quantities of high specific activity D‐ threo ‐chloramphenicol‐1‐ 3 H is described. The key step is the chromatographic separation of the compound from its 1‐epimer, produced in the Ca(B 3 H 4 ) 2 reduction of chloramphenicol ketone (D‐α‐dichloroacetyl‐amino‐β‐hydroxy‐p‐nitropropiophenone), by use of the acetonide derivative. Stereochemical aspects of the N‐bromosuccinimide oxidation of chloramphenicol to chloramphenicol ketone have been investigated, and the previously reported [1] specific rotation of chloramphenicol ketone has been corrected. The synthesis of nitrosochloramphenicol‐1‐ 3 H is described.