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【结 构 式】

【分子编号】37862

【品名】 

【CA登记号】

【 分 子 式 】C88H82N2O8

【 分 子 量 】1295.62776

【元素组成】C 81.58% H 6.38% N 2.16% O 9.88%

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:(XXV)

The condensation of the isoquinoline intermediate (IX) with the naphthaleneboronic acid intermediate (XIX) by means of palladium tetrakis(triphenylphosphine) and NaHCO3 in refluxing ethanol/toluene gives a 5:4 mixture of the (S) and (R) atropaisomers (XXIII), which, without separation, are treated with methanolic HCl to eliminate the methoxymethyl protecting groups and yield a mixture of (S) and (R) (XXIV). The dimerization of this mixture by means of silver oxide in dichloromethane affords a mixture of the (R,R), (R,S) and (S,S) dimers (XXV), which is deprotected with H2 over Pd/C in methanol/dichloromethane and submitted to HPLC to obtain the target (R,S) atropaisomer.

1 Hoye, T.R.; et al.; Total synthesis of michellamines A-C, korupensamines A-D, and ancistrobrevine B. J Org Chem 1999, 64, 19, 7184.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(S)-(XXIV) 37861 4-[(1R,3R)-2-benzyl-6,8-bis(benzyloxy)-1,3-dimethyl-1,2,3,4-tetrahydro-5-isoquinolinyl]-8-methoxy-6-methyl-1-naphthol C44H43NO4 详情 详情
(S)-(XXIII) 38319 (1R,3R)-2-benzyl-6,8-bis(benzyloxy)-5-(4,5-dimethoxy-7-methyl-1-naphthyl)-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline; benzyl (1R,3R)-2-benzyl-6-(benzyloxy)-5-(4,5-dimethoxy-7-methyl-1-naphthyl)-1,3-dimethyl-1,2,3,4-tetrahydro-8-isoquinolinyl ether C46H47NO5 详情 详情
(R)-(XXIII) 63435 2-benzyl-6,8-bis(benzyloxy)-5-[5-methoxy-4-(methoxymethoxy)-7-methyl-1-naphthyl]-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline; benzyl 2-benzyl-6-(benzyloxy)-5-[5-methoxy-4-(methoxymethoxy)-7-methyl-1-naphthyl]-1,3-dimethyl-1,2,3,4-tetrahydro-8-isoquinolinyl ether C46H47NO5 详情 详情
(R)-(XXIV) 63438 4-{1,3-dimethyl-2-(phenylmethyl)-6,8-bis[(phenylmethyl)oxy]-1,2,3,4-tetrahydro-5-isoquinolinyl}-6-methyl-8-(methyloxy)-1-naphthalenol C44H43NO4 详情 详情
(IX) 37847 benzyl (1R,3R)-2-benzyl-6-(benzyloxy)-5-iodo-1,3-dimethyl-1,2,3,4-tetrahydro-8-isoquinolinyl ether; (1R,3R)-2-benzyl-6,8-bis(benzyloxy)-5-iodo-1,3-dimethyl-1,2,3,4-tetrahydroisoquinoline C32H32INO2 详情 详情
(XIX) 37856 5-methoxy-4-(methoxymethoxy)-7-methyl-1-naphthylboronic acid C14H17BO5 详情 详情
(XXV) 37862   C88H82N2O8 详情 详情
Extended Information