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【结 构 式】

【分子编号】39414

【品名】benzyl ((2R,4S,6S)-4-[(triethylsilyl)oxy]-6-[[(triisopropylsilyl)oxy]methyl]tetrahydro-2H-pyran-2-yl)methyl ether; ([(2S,4S,6R)-6-[(benzyloxy)methyl]-4-[(triethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]methoxy)(triisopropyl)silane

【CA登记号】

【 分 子 式 】C29H54O4Si2

【 分 子 量 】522.91636

【元素组成】C 66.61% H 10.41% O 12.24% Si 10.74%

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:(XXIII)

C10-C16 Fragment: The stereocontrolled reduction of ketoester (XIX) with Me4NHB(OAc)3 in acetonitrile/AcOH gives the dihydroxyester (XX), which is dehydrated to the lactone (XXI) with PPTS in refluxing benzene. The protection of (XXI) with triethylsilyl chloride as usual affords the fully silylated lactone (XXII), which is condensed with benzyloxymethyllithium in THF and reduced with BF3/Et2O and triethylsilane giving the benzyloxymethyl derivative (XXIII). The selective deprotection of (XXIII) with BF3/Et2O yields the 4-hydroxy derivative (XXIV), which is desilylated with TBAF in THF to give the diol (XXV). The silylation of (XXV) with TBDMS-OTf and lutidine in dichloromethane yields the fully protected compound (XXVI), which is debenzylated with H2 over Pd/C in acetic acid/ethyl acetate affording the carbinol (XXVII). Finally, this compound is oxidized with oxalyl chloride and triethylamine in DMSO to provide (XXVIII), the desired C10-C16 fragment.

1 Lautens, M.; Prunet, J.A.; Carreira, E.M.; Carter, P.H.; Charette, A.B.; Evans, D.A.; Total synthesis of bryostatin 2. J Am Chem Soc 1999, 121, 33, 7540.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIX) 39410 methyl (5S)-5-hydroxy-3-oxo-6-[(triisopropylsilyl)oxy]hexanoate C16H32O5Si 详情 详情
(XX) 39411 methyl (3S,5S)-3,5-dihydroxy-6-[(triisopropylsilyl)oxy]hexanoate C16H34O5Si 详情 详情
(XXI) 39412 (4S,6S)-4-hydroxy-6-[[(triisopropylsilyl)oxy]methyl]tetrahydro-2H-pyran-2-one C15H30O4Si 详情 详情
(XXII) 39413 (4S,6S)-4-[(triethylsilyl)oxy]-6-[[(triisopropylsilyl)oxy]methyl]tetrahydro-2H-pyran-2-one C21H44O4Si2 详情 详情
(XXIII) 39414 benzyl ((2R,4S,6S)-4-[(triethylsilyl)oxy]-6-[[(triisopropylsilyl)oxy]methyl]tetrahydro-2H-pyran-2-yl)methyl ether; ([(2S,4S,6R)-6-[(benzyloxy)methyl]-4-[(triethylsilyl)oxy]tetrahydro-2H-pyran-2-yl]methoxy)(triisopropyl)silane C29H54O4Si2 详情 详情
(XXIV) 39415 (2R,4S,6S)-2-[(benzyloxy)methyl]-6-[[(triisopropylsilyl)oxy]methyl]tetrahydro-2H-pyran-4-ol C23H40O4Si 详情 详情
(XXV) 39416 (2R,4R,6S)-2-[(benzyloxy)methyl]-6-(hydroxymethyl)tetrahydro-2H-pyran-4-ol C14H20O4 详情 详情
(XXVI) 39417 [((2S,4S,6R)-6-[(benzyloxy)methyl]-4-[[tert-butyl(dimethyl)silyl]oxy]tetrahydro-2H-pyran-2-yl)methoxy](tert-butyl)dimethylsilane; benzyl [(2R,4S,6S)-4-[[tert-butyl(dimethyl)silyl]oxy]-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)tetrahydro-2H-pyran-2-yl]methyl ether C26H48O4Si2 详情 详情
(XXVII) 39418 [(2R,4S,6S)-4-[[tert-butyl(dimethyl)silyl]oxy]-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)tetrahydro-2H-pyran-2-yl]methanol C19H42O4Si2 详情 详情
(XXVIII) 39419 (2R,4R,6S)-4-[[tert-butyl(dimethyl)silyl]oxy]-6-([[tert-butyl(dimethyl)silyl]oxy]methyl)tetrahydro-2H-pyran-2-carbaldehyde C19H40O4Si2 详情 详情
Extended Information