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【结 构 式】

【分子编号】36463

【品名】(1R,2S,13R,15R,16S)-13-([[tert-butyl(diphenyl)silyl]oxy]methyl)-15-cyano-5-hydroxy-21-methoxy-22-(methoxymethoxy)-6-methyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaen-20-yl trifluoromethan

【CA登记号】

【 分 子 式 】C43H46F3N3O10SSi

【 分 子 量 】881.9991696

【元素组成】C 58.56% H 5.26% F 6.46% N 4.76% O 18.14% S 3.64% Si 3.18%

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:(XV)

The selective trifluoromethanesulfonation of the least hindered phenolic OH group of (XI) with Tf2NPh, TEA and DMAP gives monosulfonate (XII), which is selectively silylated at the primary OH group with TBDPSCl yielding silyl ether (XIII). The protection of the last OH group of (XIII) with Mom-Br and DIEA affords the fully protected intermediate (XIV), which is deallylated with Bu3SnH and PdCl2(PPh3)2 to give the intermediate (XV). The reductive methylation of the NH group of (XV) with formaldehyde and NaBH3CN yields the N-methyl derivative (XVI). The replacement of the CF3SO3 group of (XVI) by methyl is performed by treatment with Me4Sn and PdCl2(PPh3)2 in hot DMF provides the phenol (XVII), which is oxidized with (PhSeO)2O and desilylated with TBAF to give the dihydroxydienone (XVIII).

1 Gin, D.Y.; Corey, E.J.; Kania, R.S.; Enantioselective total synthesis of Ecteinascidin 743. J Am Chem Soc 1996, 118, 38, 9202-03.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 36459 allyl (1R,2S,13R,15R,16S)-5-(allyloxy)-15-cyano-20,22-dihydroxy-13-(hydroxymethyl)-21-methoxy-6-methyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaene-24-carboxylate C31H33N3O9 详情 详情
(XII) 36460 allyl (1R,2S,13R,15R,16S)-5-(allyloxy)-15-cyano-22-hydroxy-13-(hydroxymethyl)-21-methoxy-6-methyl-20-[[(trifluoromethyl)sulfonyl]oxy]-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaene-24-carbox C32H32F3N3O11S 详情 详情
(XIII) 36461 allyl (1R,2S,13R,15R,16S)-5-(allyloxy)-13-([[tert-butyl(diphenyl)silyl]oxy]methyl)-15-cyano-22-hydroxy-21-methoxy-6-methyl-20-[[(trifluoromethyl)sulfonyl]oxy]-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,1 C48H50F3N3O11SSi 详情 详情
(XIV) 36462 allyl (1R,2S,13R,15R,16S)-5-(allyloxy)-13-([[tert-butyl(diphenyl)silyl]oxy]methyl)-15-cyano-21-methoxy-22-(methoxymethoxy)-6-methyl-20-[[(trifluoromethyl)sulfonyl]oxy]-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa C50H54F3N3O12SSi 详情 详情
(XV) 36463 (1R,2S,13R,15R,16S)-13-([[tert-butyl(diphenyl)silyl]oxy]methyl)-15-cyano-5-hydroxy-21-methoxy-22-(methoxymethoxy)-6-methyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaen-20-yl trifluoromethan C43H46F3N3O10SSi 详情 详情
(XVI) 36464 (1R,2S,13R,15R,16S)-13-([[tert-butyl(diphenyl)silyl]oxy]methyl)-15-cyano-5-hydroxy-21-methoxy-22-(methoxymethoxy)-6,24-dimethyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaen-20-yl trifluorom C44H48F3N3O10SSi 详情 详情
(XVII) 36465 (1R,2S,13R,15R,16S)-13-([[tert-butyl(diphenyl)silyl]oxy]methyl)-5-hydroxy-21-methoxy-22-(methoxymethoxy)-6,20,24-trimethyl-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-4,6,11,18,20,22-hexaene-15-carbonitrile C44H51N3O7Si 详情 详情
(XVIII) 36466 (1R,2S,4R,13R,15R,16S)-4-hydroxy-13-(hydroxymethyl)-21-methoxy-22-(methoxymethoxy)-6,20,24-trimethyl-5-oxo-8,10-dioxa-14,24-diazahexacyclo[14.7.1.0(2,14).0(4,12).0(7,11).0(18,23)]tetracosa-6,11,18,20,22-pentaene-15-carbonitrile C28H33N3O8 详情 详情
Extended Information