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【结 构 式】

【分子编号】58606

【品名】7-((1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-{[(1R)-2-hydroxy-2-methyl-1-phenylpropyl]amino}ethyl)-5-(methoxymethoxy)-1,3-benzodioxol-4-yl trifluoromethanesulfonate

【CA登记号】

【 分 子 式 】C38H44F3NO9SSi

【 分 子 量 】775.9154096

【元素组成】C 58.82% H 5.72% F 7.35% N 1.81% O 18.56% S 4.13% Si 3.62%

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:(VI)

Synthesis of the amine intermediate (VIII): The condensation of 1,3-benzodioxole (I) with the didehydro morpholinone (II) by means of TFA in dichloromethane gives the chiral adduct (III), which is treated with Tf2O and pyridine in dichloromethane to yield the triflate (IV). The reductive cleavage of (IV) by means of NaBH4 in methanol affords the aminodiol (V), which is selectively monosilylated at the primary OH group with Tbdps-Cl and imidazole to provide the silyl ether (VI). The reaction of the triflate group of (VI) with MeZnCl and PdCl2(dppf) in refluxing THF gives the methylated compound (VII), which is treated with Pb(OAc)4 and NH2OH in ethanol to afford the target primary amine intermediate (VIII).

1 Abe, M.; Yanagisawa, A.; Tohma, S.; Kan, T.; Fukuyama, T.; Endo, A.; Total synthesis of ecteinascidin 743. J Am Chem Soc 2002, 124, 23, 6552.
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) 58601 5-(methoxymethoxy)-1,3-benzodioxol-4-ol C9H10O5 详情 详情
(II) 58602 (5R)-6,6-dimethyl-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one C12H13NO2 详情 详情
(III) 58603 (3R,5R)-3-[7-hydroxy-6-(methoxymethoxy)-1,3-benzodioxol-4-yl]-6,6-dimethyl-5-phenyl-2-morpholinone C21H23NO7 详情 详情
(IV) 58604 7-[(3R,5R)-6,6-dimethyl-2-oxo-5-phenylmorpholinyl]-5-(methoxymethoxy)-1,3-benzodioxol-4-yl trifluoromethanesulfonate C22H22F3NO9S 详情 详情
(V) 58605 7-((1R)-2-hydroxy-1-{[(1R)-2-hydroxy-2-methyl-1-phenylpropyl]amino}ethyl)-5-(methoxymethoxy)-1,3-benzodioxol-4-yl trifluoromethanesulfonate C22H26F3NO9S 详情 详情
(VI) 58606 7-((1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-{[(1R)-2-hydroxy-2-methyl-1-phenylpropyl]amino}ethyl)-5-(methoxymethoxy)-1,3-benzodioxol-4-yl trifluoromethanesulfonate C38H44F3NO9SSi 详情 详情
(VII) 58607 (1R)-1-({(1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[6-(methoxymethoxy)-7-methyl-1,3-benzodioxol-4-yl]ethyl}amino)-2-methyl-1-phenyl-2-propanol C38H47NO6Si 详情 详情
(VIII) 58608 (1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[6-(methoxymethoxy)-7-methyl-1,3-benzodioxol-4-yl]-1-ethanamine; (1R)-2-{[tert-butyl(diphenyl)silyl]oxy}-1-[6-(methoxymethoxy)-7-methyl-1,3-benzodioxol-4-yl]ethylamine C28H35NO5Si 详情 详情
Extended Information