tert-butyl (3R,4S)-2-oxo-4-phenyl-3-[(triethylsilyl)oxy]-1-azetidinecarboxylate -Drug Synthesis Database

【结构式】

【分子编号】49346

【品名】tert-butyl (3R,4S)-2-oxo-4-phenyl-3-[(triethylsilyl)oxy]-1-azetidinecarboxylate

【CA登记号】

【分子式】C₂₀H₃₁NO₄Si

【分子量】377.55598

【元素组成】C 63.63% H 8.28% N 3.71% O 16.95% Si 7.44%

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：(VI)

The reaction of taxol (I) with benzyloxycarbonyl chloride and DIEA in dichloromethane gives the protected compound (II), which is treated with DAST in the same solvent to yield the cyclopropa taxol (III). The hydrogenolysis of (III) with H2 over Pd/C affords compound (IV), which is deacylated with tetrabutylammonium borohydride in dichloromethane to provide the cyclopropa baccatin (V). The acylation of (V) with azetidinone (VI) by means of BuLi in THF gives the silylated taxoid (VII), which is finally desilylated with HCl in acetonitrile to afford the target compound.

参考文献中间体

合成目标

【1】 Chen, S.-H.; Farina, V. (Bristol-Myers Squibb Co.); 7,8-Cyclopropataxones. CA 2099211; EP 0577083; JP 1994179665; JP 1994179666; JP 2001199974; US 5254580 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	10595	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-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	33069-62-4	C₄₇H₅₁NO₁₄	详情	详情
(II)	49342	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[((2R,3S)-3-(benzoylamino)-2-[[(benzyloxy)carbonyl]oxy]-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		C₅₅H₅₇NO₁₆	详情	详情
(III)	49343	(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-bis(acetoxy)-16-[((2R,3S)-3-(benzoylamino)-2-[[(benzyloxy)carbonyl]oxy]-3-phenylpropanoyl)oxy]-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0(3,11).0(4,7).0(9,11)]octadec-14-en-2-yl benzoate		C₅₅H₅₅NO₁₅	详情	详情
(IV)	49344	(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-bis(acetoxy)-16-[[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0(3,11).0(4,7).0(9,11)]octadec-14-en-2-yl benzoate		C₄₇H₄₉NO₁₃	详情	详情
(V)	49345	(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-bis(acetoxy)-1,16-dihydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0(3,11).0(4,7).0(9,11)]octadec-14-en-2-yl benzoate		C₃₁H₃₆O₁₀	详情	详情
(VI)	49346	tert-butyl (3R,4S)-2-oxo-4-phenyl-3-[(triethylsilyl)oxy]-1-azetidinecarboxylate		C₂₀H₃₁NO₄Si	详情	详情
(VII)	49347	(1S,2S,3R,4S,7R,9S,11R,13R,16S)-4,13-bis(acetoxy)-16-([(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-phenyl-2-[(triethylsilyl)oxy]propanoyl]oxy)-1-hydroxy-15,18,18-trimethyl-12-oxo-6-oxapentacyclo[12.3.1.0(3,11).0(4,7).0(9,11)]octadec-14-en-2-yl benzoate		C₅₁H₆₇NO₁₄Si	详情	详情

Extended Information