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【结 构 式】

【分子编号】41101

【品名】(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3R)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate

【CA登记号】

【 分 子 式 】C47H51NO14

【 分 子 量 】853.92028

【元素组成】C 66.11% H 6.02% N 1.64% O 26.23%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VII)

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.

1 Gunatilaka, A.A.; Kingston, D.G.I.; Sarragiotto, M.H.; Ramdayal, F.D.; Synthesis and biological evaluation of novel paclitaxel (Taxol) D-ring modified analogs. J Org Chem 1999, 64, 8, 2694.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 41101 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3R)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate C47H51NO14 详情 详情
(VIII) 41102 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[((2R,3R)-3-(benzoylamino)-2-[[tert-butyl(dimethyl)silyl]oxy]-3-phenylpropanoyl)oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptade C59H79NO14Si2 详情 详情
(IX) 41103 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-12-(acetoxy)-1,2,4-trihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(triethylsilyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (2R,3R)-3-(benzoylamino)-2-[[tert-butyl(dimethyl)silyl]oxy]-3-phenylprop C50H73NO12Si2 详情 详情
(X) 41104 (1S,5S,6R,7S,10R,12S,13S,15R,18S)-15-(acetoxy)-7-hydroxy-13,17,20,20-tetramethyl-3,14-dioxo-12-[(triethylsilyl)oxy]-2,4,9-trioxapentacyclo[14.3.1.0(1,5).0(6,13).0(7,10)]icos-16-en-18-yl (2R,3R)-3-(benzoylamino)-2-[[tert-butyl(dimethyl)silyl]oxy]-3 C51H71NO13Si2 详情 详情
(XI) 41105 (1S,5S,6R,7S,10R,12S,13S,15R,18S)-15-(acetoxy)-7-[(methoxycarbonyl)oxy]-13,17,20,20-tetramethyl-3,14-dioxo-12-[(triethylsilyl)oxy]-2,4,9-trioxapentacyclo[14.3.1.0(1,5).0(6,13).0(7,10)]icos-16-en-18-yl (2R,3R)-3-(benzoylamino)-2-[[tert-butyl(dimeth C53H73NO15Si2 详情 详情
(XII) 41106   C59H79NO15Si2 详情 详情
Extended Information