2-([2-[(4-[4-[bis(2-chloroethyl)amino]phenyl]butanoyl)oxy]ethyl]amino)ethyl 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate -Drug Synthesis Database

【结构式】

【分子编号】49373

【品名】2-([2-[(4-[4-[bis(2-chloroethyl)amino]phenyl]butanoyl)oxy]ethyl]amino)ethyl 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate

【CA登记号】

【分子式】C₃₂H₄₅Cl₄N₃O₄

【分子量】677.53792

【元素组成】C 56.73% H 6.69% Cl 20.93% N 6.2% O 9.45%

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 2'-O-(triethylsilyl)paclitaxel (I) with dimethyl sulfide (DMS) and Bz2O2 in acetonitrile gives the 7-O-(methylsulfanylmethyl) derivative (II), which is condensed with chloroacetic acid (III) by means of N-iodosuccinimide (NIS) and Ag-OTf in THF to yield the 7-O-(chloroacetoxymethyl) derivative (IV). The desilylation of (IV) by means of HCl in acetonitrile affords the intermediate (V), which is finally condensed with the secondary amine (VI) by means of NaI in acetone to provide the target hybrid molecule.

参考文献中间体

合成目标

【1】 Long, B.H.; Vyas, D.M.; Fairchild, C.; Kadow, J.F.; Rose, W.C.; Johnston, K.; Wittman, M.D.; Lee, F.L.; Synthesis and antitumor activity of novel paclitaxel-chlorambucil hybrids. Bioorg Med Chem Lett 2001, 11, 6, 811.

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)	49369	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl]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		C₅₃H₆₅NO₁₄Si	详情	详情
(II)	49370	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl]oxy)-1-hydroxy-10,14,17,17-tetramethyl-9-[(methylsulfanyl)methoxy]-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate		C₅₅H₆₉NO₁₄SSi	详情	详情
(III)	11847	2-Chloroacetic acid; Chloroacetic Acid	79-11-8	C₂H₃ClO₂	详情	详情
(IV)	49371	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl]oxy)-9-[[(2-chloroacetyl)oxy]methoxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate		C₅₆H₆₈ClNO₁₆Si	详情	详情
(V)	49372	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-9-[[(2-chloroacetyl)oxy]methoxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate		C₅₀H₅₄ClNO₁₆	详情	详情
(VI)	49373	2-([2-[(4-[4-[bis(2-chloroethyl)amino]phenyl]butanoyl)oxy]ethyl]amino)ethyl 4-[4-[bis(2-chloroethyl)amino]phenyl]butanoate		C₃₂H₄₅Cl₄N₃O₄	详情	详情

Extended Information