(1R,2R,3S,5R,6S)-3,5-diazido-2-{[(2S,3R,4R,5S,6R)-3-azido-6-(azidomethyl)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-yl]oxy}-6-(benzyloxy)cyclohexanol -Drug Synthesis Database

【结构式】

【分子编号】62185

【品名】(1R,2R,3S,5R,6S)-3,5-diazido-2-{[(2S,3R,4R,5S,6R)-3-azido-6-(azidomethyl)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-yl]oxy}-6-(benzyloxy)cyclohexanol

【CA登记号】

【分子式】C₃₃H₃₆N₁₂O₆

【分子量】696.72612

【元素组成】C 56.89% H 5.21% N 24.12% O 13.78%

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：(I)

The protected azidoglycoside derivative (I) is condensed with (R)-glycidol tosylate (II) to produce the glycidyl ether (III). Epoxide opening in (III) with N,N'-dimethyl-1,4-butanediamine (IV) furnishes the diamine-linked bis azidoglycoside (V). The title compound is then obtained by simultaneous reduction of the azido groups and O benzyl groups cleavage in (V) upon catalytic hydrogenation over Pearlman's catalyst.

参考文献中间体

合成目标

【1】 Liang, C.; Duffield, J.J.; Marby, K.A.; Rabuka, D.; Romero, A.; Sgarbi, P.W.M.; Shue, Y.-K.; Sucheck, J.; Yao, S.; Zhang, Z.; Cheng, M.; Chan, F.K.; Hu, C.; Ng, S.P.; Hwang, S.-B.; The synthesis and biological activity of multivalent aminoglycoside analogues of OPT-11. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1687.

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)	62185	(1R,2R,3S,5R,6S)-3,5-diazido-2-{[(2S,3R,4R,5S,6R)-3-azido-6-(azidomethyl)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-yl]oxy}-6-(benzyloxy)cyclohexanol		C₃₃H₃₆N₁₂O₆	详情	详情
(II)	16242	(2R)oxiranylmethyl 4-methylbenzenesulfonate; (2R)-(-)-Glycidyl tosylate	113826-06-5	C₁₀H₁₂O₄S	详情	详情
(III)	62187	(2R,3R,4R,5S,6R)-3-azido-6-(azidomethyl)-4,5-bis(benzyloxy)-2-({(1R,2R,3S,4R,6S)-4,6-diazido-3-(benzyloxy)-2-[(2R)oxiranylmethoxy]cyclohexyl}oxy)tetrahydro-2H-pyran; (2R,3R,4R,5S,6R)-3-azido-6-(azidomethyl)-5-(benzyloxy)-2-({(1R,2R,3S,4R,6S)-4,6-diazido-3-(benzyloxy)-2-[(2R)oxiranylmethoxy]cyclohexyl}oxy)tetrahydro-2H-pyran-4-yl benzyl ether		C₃₆H₄₀N₁₂O₇	详情	详情
(IV)	62188	N-methyl-N-[4-(methylamino)butyl]amine; N~1~,N~4~-dimethyl-1,4-butanediamine		C₆H₁₆N₂	详情	详情
(V)	62189	(1S)-2-{[(1R,2R,3S,5R,6S)-3,5-diazido-2-{[(2R,3R,4R,5S,6R)-3-azido-6-(azidomethyl)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-yl]oxy}-6-(benzyloxy)cyclohexyl]oxy}-1-[{4-[((1S)-2-{[(1R,2R,3S,5R,6S)-3,5-diazido-2-{[(2R,3R,4R,5S,6R)-3-azido-6-(azidomethyl		C₇₆H₉₂N₂₆O₁₄	详情	详情

Extended Information