(6R)-6-([[tert-butyl(diphenyl)silyl]oxy]methyl)-5,6-dihydro-2H-pyran-2-one -Drug Synthesis Database

【结构式】

【分子编号】49636

【品名】(6R)-6-([[tert-butyl(diphenyl)silyl]oxy]methyl)-5,6-dihydro-2H-pyran-2-one

【CA登记号】

【分子式】C₂₂H₂₆O₃Si

【分子量】366.53214

【元素组成】C 72.09% H 7.15% O 13.1% Si 7.66%

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：(II)

The synthesis of dihydropyrancarbaldehyde intermediate (V) has been performed as follows: The oxidation of the selenium derivative (I) with H2O2 followed by in situ elimination gives the dihydropyranone (II), which is reduced with DIBAL to the corresponding lactol and protected as the isopropyl ether (III) by means of PPTS and isopropanol. The deprotection of the silyl ether of (III) with TBAF affords the carbinol (IV), which is finally oxidized with TPAP and NMO to provide the desired carbaldehyde intermediate (V).

参考文献中间体

合成目标

【1】 Boger, D.L.; et al.; Total synthesis of fostriecin (CI-920). J Am Chem Soc 2001, 123, 18, 4161.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	49635	(6R)-6-([[tert-butyl(diphenyl)silyl]oxy]methyl)-3-(phenylselanyl)tetrahydro-2H-pyran-2-one	C₂₈H₃₂O₃SeSi	详情	详情
(II)	49636	(6R)-6-([[tert-butyl(diphenyl)silyl]oxy]methyl)-5,6-dihydro-2H-pyran-2-one	C₂₂H₂₆O₃Si	详情	详情
(III)	49637	tert-butyl[[(2R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl]methoxy]diphenylsilane; tert-butyl(diphenyl)silyl [(2R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl]methyl ether	C₂₅H₃₄O₃Si	详情	详情
(IV)	49638	[(2R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl]methanol	C₉H₁₆O₃	详情	详情
(V)	49639	(2R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-carbaldehyde	C₉H₁₄O₃	详情	详情

Extended Information