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Synthesis of [C6-CH3-14C] and [C6-CH3-3H3]mitomycin C

✍ Scribed by Hitoshi Arai; Masaji Kasai

Publisher
John Wiley and Sons
Year
1991
Tongue
French
Weight
240 KB
Volume
29
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

A facile synthesis of the title compounds 2 and 3 is described. The key intermediate in the synthesis, 6‐demethyl‐7,7‐(ethylenedioxy)‐6‐(phenylselenenyl)mitosane (4) was synthesized in five steps from mitomycin A. Treatment of 4 with [^14^C]methyl iodide in the presence of K~2~CO~3~ afforded the [^14^C]‐labelled mitosane (5). The removal of the phenylselenenyl group of 5 and subsequent treatment of the resultant mitosane 7 with ammonia led to the desired [^14^C]mitomycin C (MMC) (2) with specific activity of 50 mCi/mmol. Similarly, [^3^H]‐labelled MMC (3) with highly specific activity of 78.4 Ci/mmol was obtained.

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