(3S,4S,5S,7R,8R,12S,14S,15R,16S,18R,26aS)-8-allyl-7,15-bis{[tert-butyl(dimethyl)silyl]oxy}-14,16-dimethoxy-20-[(4-methoxybenzyl)oxy]-3-((E)-2-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-1-methylethenyl)-4,10,12,18-tetramethyl-5-[(triisopropylsilyl)oxy]-5,6,7,8,11,12,13,14,15,16,17,18,24,25,26,26a-hexadecahydro-3H-pyrido[2,1-c][1,4]oxazacyclotricosine-1,19,21(4H,20H,23H)-trione -Drug Synthesis Database

【结构式】

【分子编号】57370

【品名】(3S,4S,5S,7R,8R,12S,14S,15R,16S,18R,26aS)-8-allyl-7,15-bis{[tert-butyl(dimethyl)silyl]oxy}-14,16-dimethoxy-20-[(4-methoxybenzyl)oxy]-3-((E)-2-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-1-methylethenyl)-4,10,12,18-tetramethyl-5-[(triisopropylsilyl)oxy]-5,6,7,8,11,12,13,14,15,16,17,18,24,25,26,26a-hexadecahydro-3H-pyrido[2,1-c][1,4]oxazacyclotricosine-1,19,21(4H,20H,23H)-trione

【CA登记号】

【分子式】C₈₂H₁₄₉NO₁₃Si₄

【分子量】1469.426

【元素组成】C 67.03% H 10.22% N 0.95% O 14.15% Si 7.65%

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：(LII)

The macrocyclization of (LI) by means of EDC and DMAP in dichloromethane gives the macrolactone (LII), which is treated with DDQ and oxidized with DMP in dichloromethane to yield the tricarbonyl compound (LIII). The cyclization and desilylation of (LIII) by means of HF in acetonitrile affords the tricyclic macrolactone (LIV), which is treated with Tes-Cl and oxidized with DMP to provide the silylated precursor (LV). Finally, this compound is desilylated with HF in acetonitrile to give the target FK-506.

参考文献中间体

合成目标

【1】 Chen, K.; Formal total synthesis of (-)-FK506. Diss Abstr Int B - Sci Eng 1993, 53, 9, 4663.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(LI)	57369	(2S)-1-{(4R,6S,7R,8S,10S,12E,14R,15R,17S,18S,19S,20E)-14-allyl-7,15-bis{[tert-butyl(dimethyl)silyl]oxy}-19-hydroxy-6,8-dimethoxy-2-[(4-methoxybenzyl)oxy]-21-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-4,10,12,18,20-pentamethyl-3-oxo-17-[(triisopropylsilyl)oxy]-12,20-henicosadienoyl}-2-piperidinecarboxylic acid	C₈₂H₁₅₁NO₁₄Si₄	详情	详情
(LII)	57370	(3S,4S,5S,7R,8R,12S,14S,15R,16S,18R,26aS)-8-allyl-7,15-bis{[tert-butyl(dimethyl)silyl]oxy}-14,16-dimethoxy-20-[(4-methoxybenzyl)oxy]-3-((E)-2-{(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl}-1-methylethenyl)-4,10,12,18-tetramethyl-5-[(triisopropylsilyl)oxy]-5,6,7,8,11,12,13,14,15,16,17,18,24,25,26,26a-hexadecahydro-3H-pyrido[2,1-c][1,4]oxazacyclotricosine-1,19,21(4H,20H,23H)-trione	C₈₂H₁₄₉NO₁₃Si₄	详情	详情
(LIII)	11564	(3S,4S,5S,7R,8R,12S,14S,15R,16S,18R,26aS)-8-Allyl-7,15-bis[[tert-butyl(dimethyl)silyl]oxy]-14,16-dimethoxy-3-((E)-2-[(1R,3R,4R)-3-methoxy-4-[(triisopropylsilyl)oxy]cyclohexyl]-1-methylethenyl)-4,10,12,18-tetramethyl-5-[(triisopropylsilyl)oxy]-5,6,7,8,11,12,13,14,15,16,17,18,24,25,26,26a-hexadecahydro-3H-pyrido[2,1-c][1,4]oxazacyclotricosine-1,19,20,21(4H,23H)-tetrone	C₇₄H₁₃₉NO₁₂Si₄	详情	详情
(LIV)	11565	(1R,9S,12S,13S,14S,16R,17R,21S,23S,24R,25S,27R)-17-Allyl-1,16-dihydroxy-23,25-dimethoxy-12-((E)-2-[(1R,3R,4R)-3-methoxy-4-[(triethylsilyl)oxy]cyclohexyl]-1-methylethenyl)-13,19,21,27-tetramethyl-14-[(triethylsilyl)oxy]-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18-ene-2,3,10-trione	C₄₄H₇₁NO₁₂	详情	详情
(LV)	11567	(1R,9S,12S,13S,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-1-hydroxy-23,25-dimethoxy-12-((E)-2-[(1R,3R,4R)-3-methoxy-4-[(triethylsilyl)oxy]cyclohexyl]-1-methylethenyl)-13,19,21,27-tetramethyl-14-[(triethylsilyl)oxy]-11,28-dioxa-4-azatricyclo[22.3.1.0(4,9)]octacos-18-ene-2,3,10,16-tetrone	C₅₆H₉₇NO₁₂Si₂	详情	详情

Extended Information