(6R)-6-((1E,3R,4R,6R,7Z)-4,6-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-8-iodo-3-methyl-1,7-octadienyl)-5,6-dihydro-2H-pyran-2-one -Drug Synthesis Database

【结构式】

【分子编号】61559

【品名】(6R)-6-((1E,3R,4R,6R,7Z)-4,6-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-8-iodo-3-methyl-1,7-octadienyl)-5,6-dihydro-2H-pyran-2-one

【CA登记号】

【分子式】C₂₆H₄₇IO₅Si₂

【分子量】622.73165

【元素组成】C 50.15% H 7.61% I 20.38% O 12.85% Si 9.02%

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 hydrolysis of the acetonide group of (XXIII) with HCl in aqueous methanol gives the dihydroxy compound (XXIV), which is monosilylated with Tbdms-OTf to yield compound (XXV). Further silylation of (XXV) with Tes-OTf affords the fully silylated compound (XXVI), which is selectively monodesilylated by means of HCl in aqueous THF/acetonitrile to provide the secondary alcohol (XXVII). Finally, this compound is condensed with the tributyltin derivative (XXVIII) by means of PdCl2(ACN)2 in DMF to furnish the target dihydropyranone intermediate (see Scheme no. 09093803b, intermediate (XXII).

参考文献中间体

合成目标

【1】 Fujii, K.; Maki, K.; Kanai, M.; Shibasaki, M.; Formal catalytic asymmetric total synthesis of fostriecin. Org Lett 2003, 5, 5, 733.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXIII)	61557	(6R)-6-{(E)-2-[(4R,5R)-5-((2R,3Z)-2-{[tert-butyl(dimethyl)silyl]oxy}-4-iodo-3-butenyl)-2,2,4-trimethyl-1,3-dioxolan-4-yl]ethenyl}-5,6-dihydro-2H-pyran-2-one	C₂₃H₃₇IO₅Si	详情	详情
(XXIV)	61558	(6R)-6-((1E,3R,4R,6R,7Z)-6-{[tert-butyl(dimethyl)silyl]oxy}-3,4-dihydroxy-8-iodo-3-methyl-1,7-octadienyl)-5,6-dihydro-2H-pyran-2-one	C₂₀H₃₃IO₅Si	详情	详情
(XXV)	61559	(6R)-6-((1E,3R,4R,6R,7Z)-4,6-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-8-iodo-3-methyl-1,7-octadienyl)-5,6-dihydro-2H-pyran-2-one	C₂₆H₄₇IO₅Si₂	详情	详情
(XXVI)	51560	[(4S)-4-benzyl-5,5-dimethyl-2-oxo-1,3-oxazolidin-3-yl]lithium	C₁₂H₁₄LiNO₂	详情	详情
(XXVII)	55495	(6R)-6-{(1E,3R,4R,6R,7Z)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-8-iodo-3-methyl-3-[(triethylsilyl)oxy]-1,7-octadienyl}-5,6-dihydro-2H-pyran-2-one	C₂₆H₄₇IO₅Si₂	详情	详情
(XXVIII)	61561	tert-butyl(diphenyl)silyl (2E,4Z)-5-(tributylstannyl)-2,4-pentadienyl ether; tert-butyl(diphenyl){[(2E,4Z)-5-(tributylstannyl)-2,4-pentadienyl]oxy}silane	C₃₃H₅₂OSiSn	详情	详情

Extended Information