【结 构 式】 |
【分子编号】35135 【品名】(4S,5S)-5-[(benzyloxy)methyl]-4-methyldihydro-2(3H)-furanone 【CA登记号】 |
【 分 子 式 】C13H16O3 【 分 子 量 】220.26824 【元素组成】C 70.89% H 7.32% O 21.79% |
合成路线1
该中间体在本合成路线中的序号:(II)Treatment of hydroxylactone (I) with benzyl bromide and silver oxide gave the corresponding benzyl ether (II). Subsequent reduction of the lactone (II) with LiAlH4 afforded the linear diol (III). Tioether (IV) was prepared by treatment of (III) with diphenyl disulfide and tributylphosphine, and the remaining hydroxyl group of (IV) was then protected as the ketal (VI) using ethyl vinyl ether (V) and pyridinium tosylate. Oxidation of (VI) to sulfone (VII) was accomplished with m-chloroperbenzoic acid. Condensation of (VII) with 2-methyl-delta-valerolactone (VIII), followed by BF3 - Et2O-catalyzed cyclization furnished spiroketal (IX). Finally, the phenylsulfonyl group of (IX) was reductively removed by means of sodium amalgam.
【1】 Oikawa, H.; et al.; Highly regio- and stereoselective reductions of spiroketals. Tetrahedron Lett 1993, 34, 33, 5303. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
12912 | 1-(Bromomethyl)benzene; Alpha-bromotoluene | 100-39-0 | C7H7Br | 详情 | 详情 | |
(I) | 35134 | (4S,5S)-5-(hydroxymethyl)-4-methyldihydro-2(3H)-furanone | C6H10O3 | 详情 | 详情 | |
(II) | 35135 | (4S,5S)-5-[(benzyloxy)methyl]-4-methyldihydro-2(3H)-furanone | C13H16O3 | 详情 | 详情 | |
(III) | 35136 | (3S,4S)-5-(benzyloxy)-3-methyl-1,4-pentanediol | C13H20O3 | 详情 | 详情 | |
(IV) | 35137 | (2S,3S)-1-(benzyloxy)-3-methyl-5-(phenylsulfanyl)-2-pentanol | C19H24O2S | 详情 | 详情 | |
(V) | 18762 | 1-Ethoxyethylene; Ethyl vinyl ether;Ethoxyethene | 109-92-2 | C4H8O | 详情 | 详情 |
(VI) | 35138 | benzyl (2S,3S)-2-(1-ethoxyethoxy)-3-methyl-5-(phenylsulfanyl)pentyl ether; 1-([[(2S,3S)-2-(1-ethoxyethoxy)-3-methyl-5-(phenylsulfanyl)pentyl]oxy]methyl)benzene | C23H32O3S | 详情 | 详情 | |
(VII) | 35139 | (3S,4S)-5-(benzyloxy)-4-(1-ethoxyethoxy)-3-methylpentyl phenyl sulfone; [(3S,4S)-5-(benzyloxy)-4-(1-ethoxyethoxy)-3-methylpentyl](dioxo)phenyl-lambda(6)-sulfane | C23H32O5S | 详情 | 详情 | |
(VIII) | 35140 | 3-methyltetrahydro-2H-pyran-2-one | C6H10O2 | 详情 | 详情 | |
(IX) | 35141 | (2S,3S,5R,6S,11R)-2-[(benzyloxy)methyl]-3,11-dimethyl-1,7-dioxaspiro[5.5]undec-5-yl phenyl sulfone; (2S,3S,5R,6S,11R)-2-[(benzyloxy)methyl]-3,11-dimethyl-5-(phenylsulfonyl)-1,7-dioxaspiro[5.5]undecane | C25H32O5S | 详情 | 详情 |