Phenyl chlorothionocarbonate

CLEAR YELLOW LIQUID

Phenyl Chlorothionoformate is used in the preparation of an bicyclic thymidine analogs as selective inhibitors of Thymidine monophosphate kinase Mycobacterium tuberculosis (TMPKmt).

O-Phenyl chlorothionoformate has been used in:

• stereodirected synthesis of optically active, ()-mintlactone
• synthesis of peptide α-thioesters having a variety of C-terminal amino acids
• synthesis of scyllo-inositol derivatives
• thionocarbonylation of unprotected thymine nucleosides
• preparation of phenoxythiocarbonyl esters of protected ribonucleosides

Purify it by dissolving in CHCl3, washing with H2O, drying (CaCl2), filtering, evaporating and distilling twice under a vacuum to give a clear yellow liquid. It is reactive and POISONOUS—work in a fume cupboard. Store it in sealed ampoules under N2. A possible impurity is O,O'-diphenyl thiocarbonate which has m 106o and remains behind in the distilling flask. [B.gemann et al. in Methoden Der Organischen Chemie (Houben-Weyl) 4th edn (E. Müller Ed.) Vol 9 Schwefel-Selen-Tellur Verbindungen pp. 807-808 1955, Rivier & Schalch Helv Chim Acta 6 612 1923, Kalson Chem Ber 20, 2384 1987, Rivier & Richard Helv Chim Acta 8 490 1925, Sch.nberg & Varga Justus Liebigs Ann Chem 483 176 1930, Sch.nberg & Vargha Chem Ber 64 1390 1931, Beilstein 6 III 609.]