(4S,5R)-2,2-bis(chloromethyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】38900

【品名】(4S,5R)-2,2-bis(chloromethyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid

【CA登记号】

【分子式】C₁₂H₁₃Cl₂NO₃

【分子量】290.14556

【元素组成】C 49.68% H 4.52% Cl 24.44% N 4.83% O 16.54%

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：(II)

The condensation of trichloroacetyl-baccatin III (I) with the oxazolidine (II) by means of DCC in toluene gives the acylated baccatin (III), which is hydrolyzed with conc. HCl yielding the N-debenzoylated taxol (IV). The acylation of the free amino group of (IV) with 1-pentenylcarbonyl chloride (V) in pyridine affords the trichloroacetylated target compound (V), which is finally deprotected with ammonium acetate in MeOH/THF.

参考文献中间体

合成目标

【1】 Choi, S.U.; Kim, D.; Roh, E.J.; Song, C.E.; Lee, C.O.; Structure-activity relationship study at the 3'-N-position of paclitaxel: synthesis and biological evaluation of 3'-N-acyl-paclitaxel analogues. Bioorg Med Chem 2002, 10, 10, 3145.
【2】 Roh, E.J.; et al.; Synthesis and biology of 3'-N-acyl-N-debenzoylpaclitaxel analogues. Bioorg Med Chem 1999, 7, 9, 2115.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	38901	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(2,2,2-trichloroacetyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate	C₃₃H₃₇Cl₃O₁₂	详情	详情
(II)	38900	(4S,5R)-2,2-bis(chloromethyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid	C₁₂H₁₃Cl₂NO₃	详情	详情
(III)	38902		C₄₅H₄₈Cl₅NO₁₄	详情	详情
(IV)	38903		C₄₂H₄₆Cl₃NO₁₄	详情	详情
(V)	38904	1-cyclopentene-1-carbonyl chloride	C₆H₇ClO	详情	详情
(VI)	38905	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-([(2R,3S)-3-[(1-cyclopenten-1-ylcarbonyl)amino]-2-hydroxy-3-phenylpropanoyl]oxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-[(2,2,2-trichloroacetyl)oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]hep	C₄₈H₅₂Cl₃NO₁₅	详情	详情

Extended Information