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【结 构 式】 
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【药物名称】TMC-435350;TMC-435;TMC-00435350;HCV-PI 【化学名称】N-[(2R,3aR,10Z,11aS,12aR,14aR)-2-[2-(4-Isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy]-5-methyl-4,14-dioxo-1,2,3,3a,4,5,6,7,8,9,11a,12,12a,13,14,14a-hexadecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecin-12a-ylcarbonyl]cyclopropanesulfonamide 【CA登记号】923604-59-5 【 分 子 式 】C38H47N5O7S2 【 分 子 量 】749.939 |
【开发单位】Tibotec Therapeutics (a division of Centocor Ortho Biotech, a subsidiary 【药理作用】HCV NS3/4A Protease Inhibitor;Anti-Hepatitis C Virus Drug |
合成路线1
Ring closing metathesis of intermediate (I) by means of Hoveyda–Grubbs first-generation catalyst in 1,2-dichloroethane at 75 °C furnishes macrocycle (II), which is then treated with LiOH in THF/MeOH/H2O to give carboxylic acid (III). Finally, activation of acid (III) by treatment with 1,1’-carbonyldiimidazole (CDI) in refluxing THF affords the oxazolidinedione derivative (IV), which is readily reacted with cyclopropylsulfonamide (V) in the presence of DBU in THF at 50 °C .
| 【1】 Raboisson, P., De Kock, H., Rosenquist, A. et al. Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350. Bioorg Med Chem Lett 2008, 18(17): 4853-8. |
| 【2】 Stokbroekx, S.C.M., Leys, C., Swinney, K.A., Wuyts, S., Horvath, A. (Tibotec Pharmaceuticals Ltd.). Polymorphic forms of a macrocyclic inhibitor of HCV. WO 2008092954. |
| 【3】 Raboisson, P.J.-M.B., De Kock, H.A., Hu, L. et al. (Tibotec Pharmaceuticals Ltd.; Medivir AB). Macrocyclic inhibitors of hepatitis C virus. CA 2616580, EP 1912999, JP 2009502889, WO 2007014926. |
| 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) | 69263 | (1S,2R)-ethyl 1-((1S,2S,4S)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate | C39H50N4O6S | 详情 | 详情 | |
| (II) | 69264 | (3aS,11aR,12aS,14aS)-ethyl 2-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-5-methyl-4,14-dioxo-1,2,3,3a,4,5,6,7,8,9,11a,12,12a,13,14,14a-hexadecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a-carboxylate | C37H46N4O6S | 详情 | 详情 | |
| (III) | 69265 | (2R,11aS,12aR,14aR)-2-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-5-methyl-4,14-dioxo-1,2,3,3a,4,5,6,7,8,9,11a,12,12a,13,14,14a-hexadecahydrocyclopenta[c]cyclopropa[g][1,6]diazacyclotetradecine-12a-carboxylic acid | C35H42N4O6S | 详情 | 详情 | |
| (IV) | 69266 | (1aS,11S,12aR,17aR)-11-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-8-methyl-1,1a,5,6,7,8,10,11,12,12a-decahydrocyclopenta[c]cyclopropa[g]oxazolo[3,4-f][1,6]diazacyclotetradecine-9,13,15,17(4H,9aH)-tetraone | C36H40N4O7S | 详情 | 详情 | |
| (V) | 68242 | cyclopropanesulfonamide；Cyclopropanesulfonyl amide | 154350-29-5 | C3H7NO2S | 详情 | 详情 |
合成路线2
Lactone acid (VI) is amidated with N-methylhex-5-enamine (VII) in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HATU) and DIEA in DMF at 0 °C. The resulting lactone amide (VIII) is opened with LiOH in THF/methanol/H2O and the intermediate carboxylic acid is then condensed with the hydrochloride of amine (IX) by means of DIAD and HATU in DMF, producing hydroxyamide (X) . Finally, alcohol (X) and quinolinol derivative (XI) are coupled under Mitsunobu conditions (PPh3, DIAD) in THF .
Alternatively, lactone acid (VI) is esterified with di-tert-butyl dicarbonate (Boc2O) in the presence of DMAP in CH2Cl2, providing the tert-butyl-protected lactone (XII), which is then opened by treatment with LiOH in dioxane/H2O at 0 °C. Amidation of the in situ-generated acid with the vinylcyclopropyl amino acid ester (IX) (in its hydrochloride form) in DMF at 0 °C gives amino acid (XIII), which is coupled with the quinoline moiety (XI) by a Mitsunobu reaction (PPh3, DIAD) in THF at 0 °C, affording adduct (XIV), with the proper configuration of the chiral center at position 3 of the cyclopentane. Subsequent deprotection of the tert-butyl ester (XIV) with triethylsilane and TFA in CH2Cl2 followed by condensation of the resulting acid with alkenylamine (VII) by means of DIAD and HATU in DMF at 0 °C yields the desired noncyclic diene (I) .
| 【1】 Raboisson, P., De Kock, H., Rosenquist, A. et al. Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350. Bioorg Med Chem Lett 2008, 18(17): 4853-8. |
| 【2】 Stokbroekx, S.C.M., Leys, C., Swinney, K.A., Wuyts, S., Horvath, A. (Tibotec Pharmaceuticals Ltd.). Polymorphic forms of a macrocyclic inhibitor of HCV. WO 2008092954. |
| 【3】 Raboisson, P.J.-M.B., De Kock, H.A., Hu, L. et al. (Tibotec Pharmaceuticals Ltd.; Medivir AB). Macrocyclic inhibitors of hepatitis C virus. CA 2616580, EP 1912999, JP 2009502889, WO 2007014926. |
| 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) | 69263 | (1S,2R)-ethyl 1-((1S,2S,4S)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate | C39H50N4O6S | 详情 | 详情 | |
| (VI) | 69267 | (1S,4S,5S)-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid | C7H8O4 | 详情 | 详情 | |
| (VII) | 69268 | N-methylhex-5-enamine;N-methylhex-5-en-1-amine | C7H15N | 详情 | 详情 | |
| (VIII) | 69269 | (1R,4S)-N-(hex-5-en-1-yl)-N-methyl-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxamide | C14H21NO3 | 详情 | 详情 | |
| (IX) | 69270 | (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate | 746657-36-3 | C8H13NO2 | 详情 | 详情 |
| (X) | 69271 | (1R,2S)-ethyl 1-((1S,2S,4R)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-hydroxycyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate | C22H34N2O5 | 详情 | 详情 | |
| (XI) | 69272 | 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-2-4-Quinolinol;(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol | 923289-21-8 | C17H18N2O2S | 详情 | 详情 |
| (XII) | 69273 | (1S,4S,5S)-tert-butyl 3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylate | C11H16O4 | 详情 | 详情 | |
| (XIII) | 69274 | (1S,2S,4S)-tert-butyl 2-(((1S,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl)carbamoyl)-4-hydroxycyclopentanecarboxylate | C19H29NO6 | 详情 | 详情 | |
| (XIV) | 69275 | (1S,2S,4S)-tert-butyl 2-(((1S,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxylate | C36H45N3O7S | 详情 | 详情 |
合成路线3
Condensation of the cyclopentanol derivative (XV) with the quinolinol derivative (XI) under Mitsunobu conditions (PPh3, DIAD) in toluene affords adduct (XVI). Methyl ester (XVI) is hydrolyzed with LiOH.H2O in THF/H2O, giving the carboxylate lithium salt (XV), which upon coupling with ethyl 1(R)-amino-2(S)-vinylcyclopropanecarboxylate (IX) in the presence of 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) in THF/H2O yields the desired intermediate (I) .
Intermediate (XVI) can also be prepared by condensation of quinolinol derivative (XI) with a different cyclopentanol derivative (XVIII) under Mitsunobu conditions (PPh3, DIAD) in toluene/THF. The benzyl ester in the resulting adduct (XIX) is converted to the corresponding carboxylic acid (XX) by treatment with triethylsilane and Pd(OAc)2 in refluxing THF or Me-THF. Finally, acid (XX) is amidated with N-methylhex-5-enamine (VII) in the presence of EEDQ in Me-THF or THF/Me-THF at 50 °C .
| 【1】 Horvath, A., Depre, D.P.M., Ormerod, D.J. (Tibotec Pharmaceuticals Ltd.). Processes and intermediates for preparing a macrocyclic protease inhibitor of HCV. WO 2008092955. |
| 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) | 69263 | (1S,2R)-ethyl 1-((1S,2S,4S)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxamido)-2-vinylcyclopropanecarboxylate | C39H50N4O6S | 详情 | 详情 | |
| (VII) | 69268 | N-methylhex-5-enamine;N-methylhex-5-en-1-amine | C7H15N | 详情 | 详情 | |
| (IX) | 69270 | (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate | 746657-36-3 | C8H13NO2 | 详情 | 详情 |
| (XI) | 69272 | 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-2-4-Quinolinol;(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol | 923289-21-8 | C17H18N2O2S | 详情 | 详情 |
| (XV) | 69276 | (1S,2S,4S)-methyl 2-(hex-5-en-1-yl(methyl)carbamoyl)-4-hydroxycyclopentanecarboxylate | C15H25NO4 | 详情 | 详情 | |
| (XVI) | 69277 | (1S,2S,4S)-methyl 2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxylate | C32H41N3O5S | 详情 | 详情 | |
| (XVII) | 69278 | lithium (1S,2S,4S)-2-(hex-5-en-1-yl(methyl)carbamoyl)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentanecarboxylate | C31H38LiN3O5S | 详情 | 详情 | |
| (XVIII) | 69279 | (1S,2S,4S)-1-benzyl 2-methyl 4-hydroxycyclopentane-1,2-dicarboxylate | C15H18O5 | 详情 | 详情 | |
| (XIX) | 69280 | (1S,2S,4S)-1-benzyl 2-methyl 4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)cyclopentane-1,2-dicarboxylate | C32H34N2O6S | 详情 | 详情 | |
| (XX) | 69281 | (1S,2S,4S)-4-((2-(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yl)oxy)-2-(methoxycarbonyl)cyclopentanecarboxylic acid | C25H28N2O6S | 详情 | 详情 |
合成路线4
Enzymatic resolution of trans-dimethyl 4-oxocyclopentane-1,2- dicarboxylate (rac-[XXI]) with pig liver esterase A (PLE-A) provides the desired (1R,2R)-enantiomer (XXI) (by selective hydrolysis of the [1S,2S]-enantiomer) . Reduction of ketone (XXI) with NaBH4 affords the meso-cyclopentanol derivative (XXII), which is finally treated with NaOH in MeOH and then with acetic anhydride in pyridine to provide the bicyclic lactone (VI) .
| 【1】 Rosenquist, A., Kvarntröm, I., Svensson, S.C.T., Classon, B., Samuelsson, B. Synthesis of enantiomerically pure trans-3,4-substituted cyclopentanols by enzymatic resolution. Acta Chem Scand 1992, 46: 1127-9. |
| 【2】 Johansson, P.O., Bäck, M., Kvarnström, I. et al. Potent inhibitors of the hepatitis C virus NS3 protease: Use of a novel P2 cyclopentane-derived template. Bioorg Med Chem 2006, 14(15): 5136-51. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (rac-(XXI) | 69282 | racemic dimethyl 4-oxocyclopentane-1,2-dicarboxylate | C9H12O5 | 详情 | 详情 | |
| (VI) | 69267 | (1S,4S,5S)-3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid | C7H8O4 | 详情 | 详情 | |
| (XXI) | 69283 | (1R,2R)-dimethyl 4-oxocyclopentane-1,2-dicarboxylate | C9H12O5 | 详情 | 详情 | |
| (XXII) | 69284 | (1R,2R)-dimethyl 4-hydroxycyclopentane-1,2-dicarboxylate | C9H14O5 | 详情 | 详情 |
合成路线5
Condensation of benzaldehyde (XXII) with ethyl glycinate hydrochloride (XXIII) in the presence of Na2SO4 and Et3N in tert-butyl methyl ether gives ethyl[(benzylidene)amino]acetate (XXIV), which upon reaction with 1,4-dibromo-2-butene (XXV) in the presence of t-BuOLi in toluene yields racemic ethyl 1-amino-2-vinylcyclopropanecarboxylate (rac-[XXVI]). Resolution of rac-(XXVI) by treatment with (+)-dibenzoyltartaric acid in EtOAc gives ethyl 1(R)-amino-2(S)-vinylcyclopropanecarboxylate (+)-dibenzoyltartrate (XXVII) salt, which is finally treated with HCl in Et2O .
Alternatively, amino ester (rac-[XXVI]) can be prepared by condensation of ethyl ester (XXVIII) with 1,4-dibromo-2-butene (XXV) in the presence of t-BuOK in THF, followed by treatment of the resulting imine (rac-[XXIX]) with HCl in Et2O and then with NaHCO3 .
| 【1】 Llinas-Brunet, M., Bailey, M.D., Cameron, D. et al. (Boehringer Ingelheim [Canada] Ltd.). Hepatitis C inhibitor tri-peptides. CA 2338946, EP 1105413, EP 2028186, JP 2002522554, US 6323180, WO 2000009543. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| rac-(XXVI) | 69285 | racemic ethyl 1-amino-2-vinylcyclopropanecarboxylate | C8H13NO2 | 详情 | 详情 | |
| rac-(XXIX) | 69287 | racemic ethyl 1-((diphenylmethylene)amino)-2-vinylcyclopropanecarboxylate | C21H21NO2 | 详情 | 详情 | |
| (IX) | 69270 | (1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate | 746657-36-3 | C8H13NO2 | 详情 | 详情 |
| (XXII) | 10498 | Benzaldehyde;Benzoic aldehyde;Phenylmethanal | 100-52-7 | C7H6O | 详情 | 详情 |
| (XXIII) | 68234 | ethyl glycinate hydrochloride；Glycine ethyl ester hydrochloride | 623-33-6 | C4H9NO2.HCl | 详情 | 详情 |
| (XXIV) | 68235 | (E)-ethyl 2-(benzylideneamino)acetate;2-(benzylideneamino)acetic acid ethyl ester；ethyl N-benzylideneglycinate；Benzylideneglycine ethyl ester；N-Benzylideneglycineethyl ester；ethyl(benzylideneamino)acetate | 40682-54-0 | C11H13NO2 | 详情 | 详情 |
| (XXV) | 18349 | (E)-1,4-dibromo-2-butene；trans-1,4-dibromo-2-butene | 821-06-7 | C4H6Br2 | 详情 | 详情 |
| (XXVII) | 69286 | ethyl 1(R)-amino-2(S)-vinylcyclopropanecarboxylate (+)-dibenzoyltartrate | 213316-32-6 | C8H13NO2 | 详情 | 详情 |
| (XXVIII) | 26772 | ethyl 2-((diphenylmethylene)amino)acetate;N-(Diphenylmethylene)glycine ethyl ester;Ethyl N-(diphenylmethylene)glycinate;ethyl 2-[(dibenzylene)amino]acetate | 69555-14-2 | C17H17NO2 | 详情 | 详情 |
合成路线6
Curtius rearrangement of 3-methoxy-2-methylbenzoic acid (XXX) by treatment with diphenylphosphonic azide (DPPA) in the presence of Et3N in toluene at 100 °C followed by t-BuOH in refluxing toluene gives N-Boc-3-methoxy-2-methylaniline (XXXI), which upon deprotection by means of TFA in CH2Cl2 and subsequent basification of the obtained TFA salt with NaHCO3 yields 3-methoxy-2-methylaniline (XXXII). Friedel–Crafts acylation of (XXXII) by a previous treatment with boron trichloride (BCl3) in CH2Cl2/xylene followed by the addition of acetonitrile and AlCl3 in CH2Cl2 at 70 °C furnishes the ortho-aminoacetophenone (XXXIII), which upon N-acylation with 4-isopropylthiazole-2-carbonyl chloride (XXXIV) in dioxane affords intermediate (XXXV). Finally, intermediate (XXXV) cyclizes in the presence of t-BuOK in t-BuOH at 100 °C .
| 【1】 Raboisson, P., De Kock, H., Rosenquist, A. et al. Structure-activity relationship study on a novel series of cyclopentane-containing macrocyclic inhibitors of the hepatitis C virus NS3/4A protease leading to the discovery of TMC435350. Bioorg Med Chem Lett 2008, 18(17): 4853-8. |
| 【2】 Stokbroekx, S.C.M., Leys, C., Swinney, K.A., Wuyts, S., Horvath, A. (Tibotec Pharmaceuticals Ltd.). Polymorphic forms of a macrocyclic inhibitor of HCV. WO 2008092954. |
| 【3】 Raboisson, P.J.-M.B., De Kock, H.A., Hu, L. et al. (Tibotec Pharmaceuticals Ltd.; Medivir AB). Macrocyclic inhibitors of hepatitis C virus. CA 2616580, EP 1912999, JP 2009502889, WO 2007014926. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XI) | 69272 | 7-methoxy-8-methyl-2-[4-(1-methylethyl)-2-thiazolyl]-2-4-Quinolinol;(4-isopropylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-ol | 923289-21-8 | C17H18N2O2S | 详情 | 详情 |
| (XXX) | 69288 | 2-methyl-m-Anisicacid;3-Methoxy-o-toluic acid;3-methoxy-2-methylbenzoic acid | 55289-06-0 | C9H10O3 | 详情 | 详情 |
| (XXXI) | 69289 | tert-butyl (3-methoxy-2-methylphenyl)carbamate | C13H19NO3 | 详情 | 详情 | |
| (XXXII) | 69290 | 3-methoxy-2-methylaniline | 19500-02-8 | C8H11NO | 详情 | 详情 |
| (XXXIII) | 69291 | 2-Methyl-3-amino-4-acetylanisole;1-(2-amino-4-methoxy-3-methylphenyl)ethanone | 912347-94-5 | C10H13NO2 | 详情 | 详情 |
| (XXXIV) | 69292 | 4-isopropylthiazole-2-carbonyl chloride | C7H8ClNOS | 详情 | 详情 | |
| (XXXV) | 69293 | N-(6-acetyl-3-methoxy-2-methylphenyl)-4-isopropylthiazole-2-carboxamide | C17H20N2O3S | 详情 | 详情 |
合成路线7
Esterification of 1,2,3,4-butanetetracarboxylic acid (XXXVI) with EtOH in the presence of H2SO4 in refluxing toluene yields the corresponding tetraethyl ester (XXXVII), which upon treatment with NaOMe in MeOH followed by HCl in refluxing H2O yields trans-4-oxocyclopentane-1,2-dicarboxylic acid (rac-[XXXVIII]). Reduction of intermediate (XXXVIII) with H2 over Rh/C in the presence of NaOH in H2O followed by treatment with H2SO4 in acetone furnishes meso-4-hydroxycyclopentane-1,2-dicarboxylic acid (rac-[XXXIX]), which upon treatment with ethyl chloroformate in the presence of Et3N in THF affords lactone acid (rac-[VI]). Acid rac-(VI) is esterified with benzyl alcohol in the presence of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) and DMAP in EtOAc. Benzyl ester (rac-[XL]) is treated with Amberlyst-15 or MsOH in MeOH, affording racemic cyclopentanol (rac-[XVIII]). Finally, racemate rac-(XVIII) is resolved by chiral HPLC, yielding the desired (R,R,R)-isomer intermediate (XVIII) .
Intermediate (XV) is prepared from intermediate (XVIII) by hydrogenolysis with H2 over Pd/C in THF or DMF and subsequent amidation of the resulting carboxylic acid (XLI) with N-methylhex-5-enamine (VII) in the presence of DIEA, HATU or O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium hexafluorophosphate (HBTU) in DMF or acetonitrile, or EDC in the presence or absence of DMAP in THF or CH2Cl2, or EEDQ in refluxing THF .
| 【1】 Llinas-Brunet, M., Bailey, M.D., Cameron, D. et al. (Boehringer Ingelheim [Canada] Ltd.). Hepatitis C inhibitor tri-peptides. CA 2338946, EP 1105413, EP 2028186, JP 2002522554, US 6323180, WO 2000009543. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| rac-(VI) | 69297 | racemic 3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylic acid | C7H8O4 | 详情 | 详情 | |
| rac-(XL) | 69300 | racemic benzyl 3-oxo-2-oxabicyclo[2.2.1]heptane-5-carboxylate | C14H14O4 | 详情 | 详情 | |
| rac-(XVIII) | 69298 | racemic 1-benzyl 2-methyl 4-hydroxycyclopentane-1,2-dicarboxylate | C15H18O5 | 详情 | 详情 | |
| (VII) | 69268 | N-methylhex-5-enamine;N-methylhex-5-en-1-amine | C7H15N | 详情 | 详情 | |
| (XV) | 69276 | (1S,2S,4S)-methyl 2-(hex-5-en-1-yl(methyl)carbamoyl)-4-hydroxycyclopentanecarboxylate | C15H25NO4 | 详情 | 详情 | |
| (XVIII) | 69299 | (1S,2S,4S)-1-benzyl 2-methyl 4-hydroxycyclopentane-1,2-dicarboxylate | C15H18O5 | 详情 | 详情 | |
| (XXXVI) | 56634 | 1,2,3,4-butanetetracarboxylic acid;1,2,3,4-Tetracarboxybutane | 1703-58-8 | C8H10O8 | 详情 | 详情 |
| (XXXVII) | 69294 | tetraethyl butane-1,2,3,4-tetracarboxylate | C16H26O8 | 详情 | 详情 | |
| (XXXVIII) | 69295 | racemic 4-oxocyclopentane-1,2-dicarboxylic acid | C7H8O5 | 详情 | 详情 | |
| (XXXIX) | 69296 | racemic 4-hydroxycyclopentane-1,2-dicarboxylic acid | C7H10O5 | 详情 | 详情 | |
| (XLI) | 69301 | (1S,2S,4S)-4-hydroxy-2-(methoxycarbonyl)cyclopentanecarboxylic acid | C8H12O5 | 详情 | 详情 |