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【结 构 式】

【分子编号】49608

【品名】3-phenyl-2,4,10-trioxatricyclo[3.3.1.1(3,7)]decane

【CA登记号】

【 分 子 式 】C13H14O3

【 分 子 量 】218.25236

【元素组成】C 71.54% H 6.47% O 21.99%

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:(III)

The reaction of cyclohexane-1,3,5-triol (I) with trimethyl orthobenzoate (II) by means of BF3/Et2O gives the cyclic orthoester (III), which is partially reduced with borane in THF to yield the alcohol (IV). Oxidation with Dess-Martin periodinane affords cyclohexanone (V), which is enantioselectively deprotonated with the chiral lithium (S,S')-alpha,alpha'-dimethyldibenzylamide (VI) in the presence of Tms-Cl in THF to provide the chiral silylated enol ether (VII). Ozonolysis of the double bond of (VII) gives the 6-oxohexanoic acid (VIII), which is reduced with NaBH4 to the corresponding hydroxyacid (IX). The methylation of (IX) with methyl iodide and K2CO3 yields the hydroxyester (X), which is oxidized with oxalyl chloride in DMSO to afford the oxoester (XI). The Wittig condensation of (XI) with decyltriphenylphosphonium bromide (XII) by means of BuLi in THF provides the unsaturated hexadecenoic ester (XIII), which is finally reduced, deprotected and cyclized by treatment with H2 over Pd/C in acetic acid to furnish the target (4S,6S)-4-hydroxy-6-undecyltetrahydrofuran-2-one (XIV). The conversion of (XIV) into tetrahydrolipstatin has already been described in scheme 11082304a.

1 Ono, S.; Endo, K.; Honda, T.; Construction of an enatiomerically pure 6-substituted 3,5-syn-dihydroxyhexanoic acid system by an enatioselective deprotonation strategy: Formal synthesis of an antiobesity agent, (-)-tetrahydrolipstatin. Chem Pharm Bull 2000, 48, 10, 1545.
2 Ghosh, A.K.; Liu, C.; A stereoselective synthesis of (-)-tetrahydrolipstatin. Chem Commun (London) 1999, 1743.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11800 1,3,5-Cyclohexanetriol; cis,cis-1,3,5-Cyclohexanetriol dihydrate 50409-12-6 C6H12O3 详情 详情
(II) 38531 dimethoxy(phenyl)methyl methyl ether; 1-(trimethoxymethyl)benzene 707-07-3 C10H14O3 详情 详情
(III) 49608 3-phenyl-2,4,10-trioxatricyclo[3.3.1.1(3,7)]decane C13H14O3 详情 详情
(IV) 49609 (1R,5S)-3-phenyl-2,4-dioxabicyclo[3.3.1]nonan-7-ol C13H16O3 详情 详情
(V) 49610 (1R,5S)-3-phenyl-2,4-dioxabicyclo[3.3.1]nonan-7-one C13H14O3 详情 详情
(VI) 49611   C16H18LiN 详情 详情
(VII) 49612 trimethyl[[(1S,3S,5R)-3-phenyl-2,4-dioxabicyclo[3.3.1]non-6-en-7-yl]oxy]silane; (1S,3S,5R)-3-phenyl-2,4-dioxabicyclo[3.3.1]non-6-en-7-yl trimethylsilyl ether C16H22O3Si 详情 详情
(VIII) 49613 2-[(2S,4S,6R)-6-formyl-2-phenyl-1,3-dioxan-4-yl]acetic acid C13H14O5 详情 详情
(IX) 49614 2-[(2S,4S,6R)-6-(hydroxymethyl)-2-phenyl-1,3-dioxan-4-yl]acetic acid C13H16O5 详情 详情
(X) 49615 methyl 2-[(2S,4S,6R)-6-(hydroxymethyl)-2-phenyl-1,3-dioxan-4-yl]acetate C14H18O5 详情 详情
(XI) 49616 methyl 2-[(2S,4S,6R)-6-formyl-2-phenyl-1,3-dioxan-4-yl]acetate C14H16O5 详情 详情
(XII) 49618 n-Decyl triphenylphosphonium bromide 32339-43-8 C28H36BrP 详情 详情
(XIII) 49617 methyl 2-[(2S,4S,6R)-2-phenyl-6-[(E)-1-undecenyl]-1,3-dioxan-4-yl]acetate C24H36O4 详情 详情
(XIV) 49598 (4S,6S)-4-hydroxy-6-undecyltetrahydro-2H-pyran-2-one C16H30O3 详情 详情
Extended Information