(2S,3S,4R)-4-{[(cyanoimino)(phenoxy)methyl]amino}-2-(dimethoxymethyl)-3-hydroxy-2-methyl-6-nitro-3,4-dihydro-2H-chromene -Drug Synthesis Database

【结构式】

【分子编号】57014

【品名】(2S,3S,4R)-4-{[(cyanoimino)(phenoxy)methyl]amino}-2-(dimethoxymethyl)-3-hydroxy-2-methyl-6-nitro-3,4-dihydro-2H-chromene

【CA登记号】

【分子式】C₂₁H₂₂N₄O₇

【分子量】442.42844

【元素组成】C 57.01% H 5.01% N 12.66% O 25.31%

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：(V)

The asymmetric epoxidation of (R)-2-methyl-6-nitro-2H-1-benzopyran-2-carbaldehyde (I) with NaOCl catalyzed by the chiral catalyst Mn(III)-Salen gives the chiral epoxide (II), which is opened by means of NH3 in hot ethanol to yield the amino alcohol (III). The reaction of (III) with diphenylcyanocarbonimidate (IV) by means of TEA in DMF/isopropanol affords the N-cyano-O-phenylisourea (V), which by reaction with benzylamine (VI) in the same solvent provides the N-cyanoguanidine (VII). Finally, the nitro group of this compound is reduced with H2 over Pd/C or NaBH4 in methanol to give the target amino derivative.

参考文献中间体

合成目标

【1】 Lee, S.; Yoo, S.; Yi, K.Y.; et al.; A novel anti-ischemic ATP-sensitive potassium channel (KATP) opener without vasorelaxation: N-(6-aminobenzopyranyl)-N-benzyl-N'-cyanoguanidine analogue. J Med Chem 2001, 44, 24, 4207.

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)	51836	(2S)-2-(dimethoxymethyl)-2-methyl-6-nitro-2H-chromene; methoxy[(2S)-2-methyl-6-nitro-2H-chromen-2-yl]methyl methyl ether		C₁₃H₁₅NO₅	详情	详情
(II)	57013	(1aS,2S,7bS)-2-(dimethoxymethyl)-2-methyl-6-nitro-1a,7b-dihydro-2H-oxireno[2,3-c]chromene; [(1aS,2S,7bS)-2-methyl-6-nitro-1a,7b-dihydro-2H-oxireno[2,3-c]chromen-2-yl](methoxy)methyl methyl ether		C₁₃H₁₅NO₆	详情	详情
(III)	51838	(2S,3S,4R)-4-amino-2-(dimethoxymethyl)-2-methyl-6-nitro-3,4-dihydro-2H-chromen-3-ol		C₁₃H₁₈N₂O₆	详情	详情
(IV)	25868	1-[(cyanoimino)(phenoxy)methoxy]benzene	107-37-9	C₁₄H₁₀N₂O₂	详情	详情
(V)	57014	(2S,3S,4R)-4-{[(cyanoimino)(phenoxy)methyl]amino}-2-(dimethoxymethyl)-3-hydroxy-2-methyl-6-nitro-3,4-dihydro-2H-chromene		C₂₁H₂₂N₄O₇	详情	详情
(VI)	15147	Benzylamine; Phenylmethanamine	100-46-9	C₇H₉N	详情	详情
(VII)	51841	N-benzyl-N''-cyano-N'-[(2S,3S,4R)-2-(dimethoxymethyl)-3-hydroxy-2-methyl-6-nitro-3,4-dihydro-2H-chromen-4-yl]guanidine		C₂₂H₂₅N₅O₆	详情	详情

Extended Information