【药物名称】BMS-188797
化学结构式(Chemical Structure):
参考文献No.581759
标题:Synthesis and biological evaluation of novel paclitaxel (Taxol) D-ring modified analogs
作者:Gunatilaka, A.A.; Ramdayal, F.D.; Sarragiotto, M.H.; Kingston, D.G.I.; Sackett, D.L.; Hamel, E.
来源:J Org Chem 1999,64(8),2694
合成路线图解说明:

In an alternative procedure, paclitaxel (VII) was sequentially protected at the 2?hydroxyl with tert-butyldimethylsilyl chloride and then at the 7-hydroxyl with triethylsilyl chloride, yielding the disilylated derivative (VIII). Selective hydrolysis of the C-2 benzoate and the C-4 acetate esters of (VIII) with Triton B afforded the triol (IX). Protection of the C-1 and C-2 hydroxy groups of (IX) with carbonyldiimidazole gave the 1,2-cyclic carbonate derivative (X). Subsequent treatment of (X) with methyl chloroformate and lithium bis(trimethylsilyl)amide introduced the 4-O-methoxycarbonyl group to furnish (XI). Opening of the cyclic carbonate group of (XI) with phenyllithium produced the benzoate ester (XII). The silyl protecting groups of (XII) were then removed by means of HF-pyridine.

参考文献No.581762
标题:Novel C-4 paclitaxel (Taxol) analogs: Potent antitumor agents
作者:Long, B.H.; Chen, S.H.; Wei, J.-M.; et al.
来源:Bioorg Med Chem Lett 1995,5(22),2741
合成路线图解说明:

The silyl-protected 4-deacetyl baccatin (I) was deprotonated with lithium bis(trimethylsilyl) amide and then condensed with methyl chloroformate to produce carbonate (II). Desilylation of (II) using HF in pyridine afforded triol (III), which was selectively resilylated at the 7-hydroxyl group to furnish (IV). Attachment of the C-13 side-chain of (IV) was achieved by treatment with lactam (V) and lithium bis(trimethylsilyl)amide, yielding ester (VI). Finally, the silyl protecting groups of (VI) were removed by treatment with HF in pyridine.

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