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【结 构 式】

【分子编号】57324

【品名】(1R,6R,10S,12S,13R,14S,16R,17R,18R,25S,28S,29R,30R)-28-[(E)-2-((1R,3R,4R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methoxycyclohexyl)-1-methylethenyl]-18-hydroxy-12,14-dimethoxy-8,10,16,29,32,32-hexamethyl-2,27,31,33,35-pentaoxa-20-azapentacyclo[28.3.1.1~13,17~.0~1,6~.0~20,25~]pentatriacont-7-ene-4,19,26-trione

【CA登记号】

【 分 子 式 】C63H93NO13Si

【 分 子 量 】1100.51586

【元素组成】C 68.76% H 8.52% N 1.27% O 18.9% Si 2.55%

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:(XXIX)

The selective desilylation of (XXV) by means of TBAF gives the diol (XXVI), which is oxidized by means of NaClO and NaClO2 to yield the hydroxyacid (XXVII), which is methylated with diazomethane to afford the methyl ester (XXVIII). The cyclization of (XXVIII) by means of LiOH and Tes-OTf provides the macrocyclic alpha-hydroxy ketonic intermediate (XXIX), which is oxidized with DMP to the alpha diketonic intermediate (XXX).

1 Gleason, J.L.; The total synthesis of FK-506 and its spiroketal analogs. Diss Abstr Int B - Sci Eng 1994, 54, 12, Part 1, 6206.
2 Ireland, R.E.; et al.; A total synthesis of FK-506. J Org Chem 1996, 61, 20, 6856.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXV) 57320 2-[(1S,2E)-1-[(1R)-1-((4S,6R,11R)-11-{(E,4S,6S)-6-[(2R,3S,5R,6R)-6-((1S)-1,2-bis{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-methoxy-5-methyltetrahydro-2H-pyran-2-yl]-6-methoxy-2,4-dimethyl-1-hexenyl}-2,2-dimethyl-9-oxo-1,3,7-trioxaspiro[5.5]undec-4-yl)ethyl]-3-((1R,3R,4R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methoxycyclohexyl)-2-methyl-2-propenyl] 1-(tert-butyl) (2S)-1,2-piperidinedicarboxylate C80H133NO15Si3 详情 详情
(XXVI) 57321 1-(tert-butyl) 2-((1S,2E)-3-((1R,3R,4R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methoxycyclohexyl)-1-{(1R)-1-[(4S,6R,11R)-11-((E,4S,6S)-6-{(2R,3S,5R,6R)-6-[(1S)-1,2-dihydroxyethyl]-3-methoxy-5-methyltetrahydro-2H-pyran-2-yl}-6-methoxy-2,4-dimethyl-1-hexenyl)-2,2-dimethyl-9-oxo-1,3,7-trioxaspiro[5.5]undec-4-yl]ethyl}-2-methyl-2-propenyl) (2S)-1,2-piperidinedicarboxylate C68H105NO15Si 详情 详情
(XXVII) 57322 (2R)-2-[(2R,3R,5S,6R)-6-((1S,3S,5E)-6-{(4S,6R,11R)-4-[(1R,2S,3E)-2-({[(2S)-1-(tert-butoxycarbonyl)piperidinyl]carbonyl}oxy)-4-((1R,3R,4R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methoxycyclohexyl)-1,3-dimethyl-3-butenyl]-2,2-dimethyl-9-oxo-1,3,7-trioxaspiro[5.5]undec-11-yl}-1-methoxy-3,5-dimethyl-5-hexenyl)-5-methoxy-3-methyltetrahydro-2H-pyran-2-yl]-2-hydroxyethanoic acid C68H103NO16Si 详情 详情
(XXVIII) 57323 1-(tert-butyl) 2-((1S,2E)-3-((1R,3R,4R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methoxycyclohexyl)-1-{(1R)-1-[(4S,6R,11R)-11-((E,4S,6S)-6-{(2R,3S,5R,6R)-6-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-3-methoxy-5-methyltetrahydro-2H-pyran-2-yl}-6-methoxy-2,4-dimethyl-1-hexenyl)-2,2-dimethyl-9-oxo-1,3,7-trioxaspiro[5.5]undec-4-yl]ethyl}-2-methyl-2-propenyl) (2S)-1,2-piperidinedicarboxylate C69H105NO16Si 详情 详情
(XXIX) 57324 (1R,6R,10S,12S,13R,14S,16R,17R,18R,25S,28S,29R,30R)-28-[(E)-2-((1R,3R,4R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methoxycyclohexyl)-1-methylethenyl]-18-hydroxy-12,14-dimethoxy-8,10,16,29,32,32-hexamethyl-2,27,31,33,35-pentaoxa-20-azapentacyclo[28.3.1.1~13,17~.0~1,6~.0~20,25~]pentatriacont-7-ene-4,19,26-trione C63H93NO13Si 详情 详情
(XXX) 57325 (1R,6R,10S,12S,13R,14S,16R,17R,25S,28S,29R,30R)-28-[(E)-2-((1R,3R,4R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methoxycyclohexyl)-1-methylethenyl]-12,14-dimethoxy-8,10,16,29,32,32-hexamethyl-2,27,31,33,35-pentaoxa-20-azapentacyclo[28.3.1.1~13,17~.0~1,6~.0~20,25~]pentatriacont-7-ene-4,18,19,26-tetrone C63H91NO13Si 详情 详情
Extended Information