(2R,3R)-3-cyclopropyl-2-oxiranecarboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】26476

【品名】(2R,3R)-3-cyclopropyl-2-oxiranecarboxylic acid

【CA登记号】

【分子式】C₆H₈O₃

【分子量】128.12772

【元素组成】C 56.25% H 6.29% O 37.46%

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：(XVII)

In a related procedure, epoxy carboxylic acid (XVII) was either obtained by basic hydrolysis of ethyl ester (XV) or by hydrogenolysis of benzyl ester (XVI). Alternatively, acid (XVII) was isolated as the dimethylaminopyridinium salt. Coupling of (XVII) with protected taxane (XI) provided ester (XVIII). Then, epoxide opening in (XVIII) with either NaN3 or Bu3SnN3 and ZnI2 gave azide (XIX). Subsequent hydrogenation of (XIX) produced amine (XX), which was treated with Boc2O to yield intermediate (XIII).

参考文献中间体

合成目标

【1】 Tsujihari, K.; Hashiyama, T.; Ohashi, M.; Nakanishi, N. (Tanabe Seiyaku Co., Ltd.); Baccatin derivs. and processes for preparing the same. CA 2162759; EP 0712854; JP 1997151181; US 5589502 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XI)	23892	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-1,15-dihydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate	C₃₅H₃₈Cl₆O₁₄	详情	详情
(XIII)	26472	methyl (9S,12S)-4-methoxy-12-[[(2S,5S,8S,11R)-5-(4-methoxybenzyl)-2,6,8,11,15,15-hexamethyl-4,7,10,13-tetraoxo-14-oxa-3,6,9,12-tetraazahexadec-1-anoyl](methyl)amino]-11-oxo-2-oxa-10-azatricyclo[12.2.2.1(3,7)]nonadeca-1(16),3(19),4,6,14,17-hexaene-9-carboxylate	C₄₉H₅₉Cl₆NO₁₈	详情	详情
(XV)	26467	methyl (2R,3R)-3-cyclopropyl-2-oxiranecarboxylate	C₇H₁₀O₃	详情	详情
(XVI)	26475	benzyl (2R,3R)-3-cyclopropyl-2-oxiranecarboxylate	C₁₃H₁₄O₃	详情	详情
(XVII)	26476	(2R,3R)-3-cyclopropyl-2-oxiranecarboxylic acid	C₆H₈O₃	详情	详情
(XVIII)	26477	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-2-(benzoyloxy)-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-15-yl (2R,3R)-3-cyclopropyl-2-oxiranecarboxylate	C₄₁H₄₄Cl₆O₁₆	详情	详情
(XIX)	26478	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-15-[[(2R,3S)-3-azido-3-cyclopropyl-2-hydroxypropanoyl]oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate	C₄₁H₄₅Cl₆N₃O₁₆	详情	详情
(XX)	26479	(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetoxy)-15-[[(2R,3S)-3-amino-3-cyclopropyl-2-hydroxypropanoyl]oxy]-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9,12-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate	C₄₁H₄₇Cl₆NO₁₆	详情	详情

Extended Information