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【结 构 式】

【分子编号】46672

【品名】(2S,4E)-2-[(3aS,7S,7aR)-7-hydroxy-3a-methyl-3a,4,5,6,7,7a-hexahydro-1H-inden-3-yl]-6-ethyl-6-[(triethylsilyl)oxy]-4-octenyl 4-methylbenzenesulfonate

【CA登记号】

【 分 子 式 】C33H54O5SSi

【 分 子 量 】590.94026

【元素组成】C 67.07% H 9.21% O 13.54% S 5.43% Si 4.75%

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:(XI)

The indenone intermediate (XIII) has been obtained as follows: The silylation of 3-methyl-1-pentyn-3-ol (I) with Tes-Cl and DMAP in DMF gives the silyl ether (II), which is condensed with paraformaldehyde and n-BuLi in THF to yield the propargyl alcohol (III). Partial reduction of (III) with Red-Al in THF affords the allyl alcohol (IV), which is treated with Ts-Cl and DMAP in dichloromethane to provide the allyl chloride (V). The condensation of (V) with the unsaturated ester (VI) (obtained by Wittig condensation of perhydroindanone (VII) with triethyl phosphonoacetate (VIII) by means of EtONa) by means of BuLi and dicyclohexylamine in HMPA gives the octenoic ester (IX), which is reduced with LiAlH4, yielding the corresponding primary alcohol (X). The reaction of (X) with TsCl and pyridine affords the tosylate (XI), which is reduced with LiBEt3H in THF with simultaneous opening of the epoxide ring to provide the hexahydroindenol (XII). Finally, this compound is oxidized with pyridinium dichromate (PDC), yielding the target hexahydroindenone intermediate (XIII).

1 Radinov, R.N.; Daniewski, A.R. (F. Hoffmann-La Roche AG); Process for preparing anti-osteoporotic agents. EP 1048661; JP 2000336094 .
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) 46664 3-ethyl-1-pentyn-3-ol 6285-06-9 C7H12O 详情 详情
(II) 46665 [(1,1-diethyl-2-propynyl)oxy](triethyl)silane; 1,1-diethyl-2-propynyl triethylsilyl ether C13H26OSi 详情 详情
(III) 46666 4-ethyl-4-[(triethylsilyl)oxy]-2-hexyn-1-ol C14H28O2Si 详情 详情
(IV) 46667 (E)-4-ethyl-4-[(triethylsilyl)oxy]-2-hexen-1-ol C14H30O2Si 详情 详情
(V) 46668 (E)-4-chloro-1,1-diethyl-2-butenyl triethylsilyl ether; [[(E)-4-chloro-1,1-diethyl-2-butenyl]oxy](triethyl)silane C14H29ClOSi 详情 详情
(VI) 46669 ethyl 2-[(1aS,3aS,6aR,6bR)-3a-methyloctahydro-4H-indeno[4,5-b]oxiren-4-ylidene]acetate C14H20O3 详情 详情
(VII) 45538 (1aS,3aS,6aR,6bR)-3a-methyloctahydro-4H-indeno[4,5-b]oxiren-4-one C10H14O2 详情 详情
(VIII) 10019 Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate 867-13-0 C8H17O5P 详情 详情
(IX) 46670 ethyl (2S,4E)-2-[(1aS,3aS,6aR,6bR)-3a-methyl-2,3,3a,6,6a,6b-hexahydro-1aH-indeno[4,5-b]oxiren-4-yl]-6-ethyl-6-[(triethylsilyl)oxy]-4-octenoate C28H48O4Si 详情 详情
(X) 46671 (3aS,7S,7aR)-3-[(1S,3E)-5-ethyl-1-(hydroxymethyl)-5-[(triethylsilyl)oxy]-3-heptenyl]-3a-methyl-3a,4,5,6,7,7a-hexahydro-1H-inden-7-ol C26H48O3Si 详情 详情
(XI) 46672 (2S,4E)-2-[(3aS,7S,7aR)-7-hydroxy-3a-methyl-3a,4,5,6,7,7a-hexahydro-1H-inden-3-yl]-6-ethyl-6-[(triethylsilyl)oxy]-4-octenyl 4-methylbenzenesulfonate C33H54O5SSi 详情 详情
(XII) 46673 (3aS,7S,7aR)-3-[(1S,3E)-5-ethyl-1-methyl-5-[(triethylsilyl)oxy]-3-heptenyl]-3a-methyl-3a,4,5,6,7,7a-hexahydro-1H-inden-7-ol C26H48O2Si 详情 详情
(XIII) 46674 (3aR,7aS)-1-[(1S,3E)-5-ethyl-1-methyl-5-[(triethylsilyl)oxy]-3-heptenyl]-7a-methyl-3,3a,5,6,7,7a-hexahydro-4H-inden-4-one C26H46O2Si 详情 详情
Extended Information