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【结 构 式】

【分子编号】36861

【品名】 

【CA登记号】

【 分 子 式 】C15H14BF3O5

【 分 子 量 】342.0793696

【元素组成】C 52.67% H 4.13% B 3.16% F 16.66% O 23.39%

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:(XL)

The enzymatic resolution of the tricyclic carboxylate (XXIX) with chiralzyme L-2 and vinyl acetate gives the monoacetate (XXX) and the dihydroxy compound (XXXI) that are easily separated. The monosilylation of the less hindered OH group of (XXXI) with TBDMS-Cl and imidazole in DMF gives the monosilylated compound (XXXII), which is acylated with acetyl chloride, TEA and DMAP in dichloromethane yielding the monoacetate (XXXIII). The desilylation of (XXXIII) with TBAF in THF affords the secondary alcohol (XXXIV), which is oxidized with ammonium formate and PdCl2(PPh3)2 in acetonitrile to give the unsaturated ketone (XXXV). The epoxidation of the double bond of (XXXV) with H2O2 and Triton B in THF yields the ketoepoxide (XXXVI), which is reduced with NaBH4 in methanol to the epoxy alcohol (XXXVII). The esterification of (XXXVII) with benzoyl chloride affords the benzoate (XXXVIII), which is submitted to thermolysis at 300 C in diphenyl ether to provide the cyclohexenecarboxylate (XXXIX).The reaction of (XXXIX) with BF3 ethearate in toluene gives, through the nonisolable oxonium intermediate (XL), the monobenzoate (XLI), which is debenzoylated with K2CO3 in methanol to provide the methyl ester (XLII) of the target compound. Finally, this compound is hydrolyzed with KOH in THF.

1 Yoshida, N.; Ogasawara, K.; An enatioconvergent route to (-)-shikimic acid via a palladium-mediated elimination reaction. Org Lett 2000, 2, 10, 1461.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXIX),(XXXI) 36851 methyl (2R,3R,6S)-3,6-dihydroxytricyclo[6.2.1.0(2,7)]undeca-4,9-diene-2-carboxylate C13H16O4 详情 详情
(XIV) 29907 (3R,4S,5R)-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid; Shikimic acid 138-59-0 C7H10O5 详情 详情
(XXX) 36852 methyl (2S,3S,6R)-6-(acetoxy)-3-hydroxytricyclo[6.2.1.0(2,7)]undeca-4,9-diene-2-carboxylate C15H18O5 详情 详情
(XXXII) 36853 methyl (2R,3R,6S)-6-[[tert-butyl(dimethyl)silyl]oxy]-3-hydroxytricyclo[6.2.1.0(2,7)]undeca-4,9-diene-2-carboxylate C19H30O4Si 详情 详情
(XXXIII) 36854 methyl (2R,3R,6S)-3-(acetoxy)-6-[[tert-butyl(dimethyl)silyl]oxy]tricyclo[6.2.1.0(2,7)]undeca-4,9-diene-2-carboxylate C21H32O5Si 详情 详情
(XXXIV) 36855 methyl (2R,3R,6S)-3-(acetoxy)-6-hydroxytricyclo[6.2.1.0(2,7)]undeca-4,9-diene-2-carboxylate C15H18O5 详情 详情
(XXXV) 36856 methyl (2R)-6-oxotricyclo[6.2.1.0(2,7)]undeca-4,9-diene-2-carboxylate C13H14O3 详情 详情
(XXXVI) 36857 methyl (2R,4R,6R)-7-oxo-5-oxatetracyclo[7.2.1.0(2,8).0(4,6)]dodec-10-ene-2-carboxylate C13H14O4 详情 详情
(XXXVII) 36858 methyl (2R,4R,6S,7R)-7-hydroxy-5-oxatetracyclo[7.2.1.0(2,8).0(4,6)]dodec-10-ene-2-carboxylate C13H16O4 详情 详情
(XXXVIII) 36859 methyl (2R,4R,6R,7R)-7-(benzoyloxy)-5-oxatetracyclo[7.2.1.0(2,8).0(4,6)]dodec-10-ene-2-carboxylate C20H20O5 详情 详情
(XXXIX) 36860 methyl (1R,5R,6R)-5-(benzoyloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylate C15H14O5 详情 详情
(XL) 36861   C15H14BF3O5 详情 详情
(XLI) 36862 (1R,5R,6S)-5,6-dihydroxy-3-(methoxycarbonyl)-2-cyclohexen-1-yl benzoate C15H16O6 详情 详情
(XLII) 29908 methyl (3R,4S,5R)-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate C8H12O5 详情 详情
Extended Information