2-amino-N-[(2R,3R,4R,5R,6S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-6-(9H-purin-6-ylamino)tetrahydro-2H-pyran-3-yl]acetamide -Drug Synthesis Database

【结构式】

【分子编号】54229

【品名】2-amino-N-[(2R,3R,4R,5R,6S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-6-(9H-purin-6-ylamino)tetrahydro-2H-pyran-3-yl]acetamide

【CA登记号】n/a

【分子式】C₁₄H₂₁N₇O₆

【分子量】383.36432

【元素组成】C 43.86% H 5.52% N 25.58% O 25.04%

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 hydrolysis of the spicamycin mixture (I) with R = alkyl by means of HCl in alcohol or water gives 6-(spicaminylamino)purine (II). (The hydrolysis can also be performed with other inorganic acids such as H2SO4 or organic ones such as acetic acid or formic acid.) The condensation of (II) with N-(tert-butoxycarbonyl)glycine (III) by the active ester method yields the protected glycyl derivative (IV), which is deprotected with TFA (or methanolic HCl) to afford the glycyl derivative (V). Finally, this compound is condensed with tetradeca-2(E),4(E)-dienoic acid (VI) by the active ester method to provide the target carboxamide derivative.

参考文献中间体

合成目标

【1】 Otake, N.; Kawai, H.; Kawasaki, T.; Odagawa, A.; Kamishohara, M.; Sakai, T. (Kirin Brewery Co., Ltd.); Spicamycin derivs. and the use thereof. EP 0525479; JP 1993186494; US 5461036; US 5631238 .

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)	54226	N-(2-{[(2R,3R,4R,5R,6S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-6-(9H-purin-6-ylamino)tetrahydro-2H-pyran-3-yl]amino}-2-oxoethyl)-14-methylpentadecanamide	n/a	C₃₀H₅₁N₇O₇	详情	详情
(II)	54227	(2S,3R,4R,5R,6R)-5-amino-6-[(1R)-1,2-dihydroxyethyl]-2-(9H-purin-6-ylamino)tetrahydro-2H-pyran-3,4-diol	n/a	C₁₂H₁₈N₆O₅	详情	详情
(III)	18066	N-alpha-t-BOC-glycine; 2-[(tert-butoxycarbonyl)amino]acetic acid	4530-20-5	C₇H₁₃NO₄	详情	详情
(IV)	54228	tert-butyl 2-{[(2R,3R,4R,5R,6S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-6-(9H-purin-6-ylamino)tetrahydro-2H-pyran-3-yl]amino}-2-oxoethylcarbamate	n/a	C₁₉H₂₉N₇O₈	详情	详情
(V)	54229	2-amino-N-[(2R,3R,4R,5R,6S)-2-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxy-6-(9H-purin-6-ylamino)tetrahydro-2H-pyran-3-yl]acetamide	n/a	C₁₄H₂₁N₇O₆	详情	详情
(VI)	54230	5,8-Tetradecadienoic acid	10390-16-6	C₁₄H₂₄O₂	详情	详情

Extended Information