- Synthesis of TA 077
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TA 077 (CAS NO.: ), with its systematic name of , N-(2-chloroethyl)-N'-(4-O-alpha-D-glucopyranosyl-beta-D-glucopyranosyl)-N'-(2-methylpropyl)-N-nitroso-, could be produced through many synthetic methods.
Following is one of the reaction routes: Maltose (I) could react with isobutylamine (II) in the presence of methanol at 65 C to produce isobutylmaltosylamine (III), which is condensed with 2-chloroethyl isocyanate (IV) yielding 1-(2-chloroethyl)-3-isobutyl-3-D-maltosylurea (V). The nitrosation of (V) with dinitrogen tetroxide in THF in the presence of sodium acetate gives 1-(2-chloroethyl)-3-isobutyl-3-(beta-D-heptanitrosomaltosyl)-1-nitrosourea (VI). The nitrous esters of (VI) can be decomposed without affecting the N-nitroso group by addition of methanol under acidic conditions to give TA-077 in good yield.
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