【药物名称】IsoddA-(S,S), 191W91
化学结构式(Chemical Structure):
参考文献No.547381
标题:Synthesis of purine and pyrimidine isodideoxynucleosides from (S)-glycydol using iodoetherification as key step. Synthesis of (S,S)-iso-ddA
作者:D韆z, Y.; et al.
来源:J Org Chem 1999,64(17),6508
合成路线图解说明:

The reaction of silylated (S)-glycidol (I) with the vinyl copper compound (II) in ethyl ether gives the monosilylated unsaturated diol (III), which is desilylated with Bu4NF in THF yielding the diol (IV). The cyclization of (IV) by means of I2 and NaHCO3 in acetonitrile affords a mixture of the cis and trans diastereomers from which the trans isomer (V) was isolated. The acylation of (V) with potassium 4-nitrobenzoate (VI) in DMSO/18-crown-6 yields the 4-nitrobenzoyl ester (VII), which is condensed with adenine (VIII) by means of DEAD and triphenylphosphine in DMF providing the 4-nitrobenzoyl percursor (IX). Finally, (IX) is debenzoylated with NaOMe in methanol.

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