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【结 构 式】 
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【分子编号】41006 【品名】(2S)-oxiranylmethyl trityl ether; (2S)-2-[(trityloxy)methyl]oxirane 【CA登记号】 |
【 分 子 式 】C22H20O2 【 分 子 量 】316.3996 【元素组成】C 83.52% H 6.37% O 10.11% |
合成路线1
该中间体在本合成路线中的序号：(II)Treatment of (R)-1-chloro-2,3-propanediol (I) with either K2CO3 or Cs2CO3 in CH2Cl2, followed by O-protection with Trt-Cl and Et3N in CH2Cl2, yields (S)-trityl glycidol (II). Alternatively, derivative (II) can also be obtained either by direct O-protection of (R)-glycidol (III) by means of Trt-Cl and Et3N in refluxing CH2Cl2 or by cyclization of protected propanediol derivative (IV)--obtained from treatment of compound (I) with Trt-Cl and Et3N in CH2Cl2--by means of KOH in EtOH. Reaction of (S)-trityl glycidol (II) with vinyl magnesium bromide (V) by means of CuI in THF provides (S)-1-(triphenylmethoxy)-4-penten-2-ol (VI), which is then condensed with allyl bromide (VII) with KOtBu or NaH in THF to afford compound (VIII). Ozonolysis of (VIII) in CH2Cl2/MeOH, followed by reductive quench with NaBH4 in NaOH, gives (S)-3-(2-hydroxyethoxy)-4-(triphenylmethoxy)-1-butanol (IX), which is then treated with MsCl/Et3N in CH2Cl2 to yield bismesylate (X). Coupling of compound (X) with 2,3-bis(1H-indol-3-yl)-N-methylmaleimide (XI) [obtained by treatment of dichloromaleic anhydride (XII) with methylamine hydrochloride by means of NaOMe in HOAc to furnish dichloro-N-methylmaleimide (XIII), followed by Grignard reaction of (XIII) with indole (XIV) in toluene/THF by means of EtMgBr in Et2O] by means of Cs2CO3 in DMF gives the 14-membered macrocycle (XV).
| 【1】 Faul, M.M.; Sullivan, K.A.; Neel, D.A.; Krumrich, C.A.; Jirousek, M.R.; Winneroski, L.L.; Gillig, J.R.; Rito, C.J.; Macrocyclic bisindolylmaleimides: Synthesis by inter- and intramolecular alkylation. J Org Chem 1998, 63, 6, 1961. |
| 【2】 Engel, G.L.; Farid, N.A.; Faul, M.M.; Jirousek, M.R.; Richardson, L.A.; Winneroski, L.L. Jr. (Eli Lilly and Company); Protein kinase C inhibitor. EP 0776895; JP 1999500149; US 5710145; WO 9718809 . |
| 【3】 Faul, M.M.; Winneroski, L.L. Jr.; Krumrich, C.A. (Eli Lilly and Company); Intermediates and their use to prepare N,N'-bridged bisindolylmaleimides. US 5721272 . |
| 【4】 Rito, C.J.; Mcdonald, J.H. III; Jirousek, M.R.; Winneroski, L.L. Jr.; Heath, W.F. Jr.; Faul, M.M. (Eli Lilly and Company); Improved synthesis of bisindolylmaleimides. EP 0657411; US 5541347 . |
| 【5】 Faul, M.M.; Winneroski, L.L. Jr.; Krumrich, C.A. (Eli Lilly and Company); Intermediates and their use to prepare N,N'-bridged bisindolylmaleimides. EP 0776899 . |
| 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) | 49696 | (S)-(+)-Alpha-Chlorohydrin; (S)-(+)-3-Chloro-1,2-propanediol; (S)-3-Chloro-1,2-propanediol | 60827-45-4 | C3H7ClO2 | 详情 | 详情 |
| (II) | 41006 | (2S)-oxiranylmethyl trityl ether; (2S)-2-[(trityloxy)methyl]oxirane | C22H20O2 | 详情 | 详情 | |
| (III) | 19241 | (2S)oxiranylmethanol | 60456-23-7 | C3H6O2 | 详情 | 详情 |
| (IV) | 51942 | (2R)-1-chloro-3-(trityloxy)-2-propanol | C22H21ClO2 | 详情 | 详情 | |
| (V) | 16524 | bromo(vinyl)magnesium | 1826-67-1 | C2H3BrMg | 详情 | 详情 |
| (VI) | 41007 | (2S)-1-(trityloxy)-4-penten-2-ol | C24H24O2 | 详情 | 详情 | |
| (VII) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (VIII) | 41008 | 1-[[[(2S)-2-(allyloxy)-4-pentenyl]oxy](diphenyl)methyl]benzene; allyl (1S)-1-[(trityloxy)methyl]-3-butenyl ether | C27H28O2 | 详情 | 详情 | |
| (IX) | 41010 | (3S)-3-(2-hydroxyethoxy)-4-(trityloxy)-1-butanol | C25H28O4 | 详情 | 详情 | |
| (X) | 51943 | (7S)-2,11-dimethyl-2,11-dimethylene-7-[(trityloxy)methyl]-3,6,10-trioxa-2lambda(6),11lambda(6)-dithia-1,11-dodecadiene; 2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]ethyl (1S)-3-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-1-[(trityloxy)methyl]propyl ether | C31H40O4S2 | 详情 | 详情 | |
| (XI) | 51012 | 5-(tert-butyl) 1-(2,3,5,6-tetrafluorophenyl) (2S)-2-[[(2S)-2-[[(benzyloxy)carbonyl]amino]-5-(tert-butoxy)-5-oxopentanoyl]amino]pentanedioate | C32H38F4N2O9 | 详情 | 详情 | |
| (XII) | 21947 | 3,4-dichloro-2,5-furandione | 1122-17-4 | C4Cl2O3 | 详情 | 详情 |
| (XIII) | 41029 | 3,4-dichloro-1-methyl-1H-pyrrole-2,5-dione | C5H3Cl2NO2 | 详情 | 详情 | |
| (XIV) | 15292 | Indole; 1H-indole | 120-72-9 | C8H7N | 详情 | 详情 |
| (XV) | 41016 | (18S)-4-methyl-18-[(trityloxy)methyl]-17-oxa-4,14,21-triazahexacyclo[19.6.1.1(7,14).0(2,6).0(8,13).0(22,27)]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaene-3,5-dione | C46H39N3O4 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(III)Protection of (R)-glycidol (I) with trityl chloride (II) and TEA in dichloromethane gives the trityl ether (III), which is condensed with vinylmagnesium bromide (IV) in THF to yield the pentenol (V). The alkylation of (V) with allyl bromide (VI) by means of NaH in THF affords the allyl ether (VII), which is oxidized with O3 in methanol/dichloromethane, giving dialdehyde (VIII). Reduction of (VIII) with NaBH4 in ethanol provides diol (IX), which is treated with mesyl chloride and TEA in dichloromethane to afford the fully protected alcohol (X). Cyclization of (X) with 3,4-bis(3-indolyl)-1-methyl-2,5-dihydro-1H-pyrrole-2,5-dione (XI) by means of Cs2CO3 in DMF yields the hexacyclic compound (XII), which is N-demethylated by reaction with KOH in refluxing ethanol to give the hexacyclic furan derivative (XIII), which is then treated with hexamethyldisilazane (HMDS) in hot methanol to afford the hexacyclic demethylated pyrrole (XIV). Elimination of the trityl protecting group of (XIV) with HCl in dichloromethane gives the methanol derivative (XV), which is treated with Br2, pyridine and triphenyl phosphite in dichloromethane to yield the bromomethyl derivative (XVI). Finally, this compound is treated with dimethylamine in DMF to provide LY-333531. Alternatively, compound (XV) is treated with methanesulfonic anhydride and pyridine in THF, giving the mesylate (XVII), which is then treated with dimethylamine as before.
| 【1】 Faul, M.M.; Sullivan, K.A.; Neel, D.A.; Krumrich, C.A.; Jirousek, M.R.; Winneroski, L.L.; Gillig, J.R.; Rito, C.J.; Macrocyclic bisindolylmaleimides: Synthesis by inter- and intramolecular alkylation. J Org Chem 1998, 63, 6, 1961. |
| 【2】 Sorbera, L.A.; Rabasseda, X.; Silvestre, J.S.; Castañer, J.; LY-333531 Mesylate Hydrate. Drugs Fut 2000, 25, 10, 1017-1026. |
| 【3】 Engel, G.L.; Farid, N.A.; Faul, M.M.; Jirousek, M.R.; Richardson, L.A.; Winneroski, L.L. Jr. (Eli Lilly and Company); Protein kinase C inhibitor. EP 0776895; JP 1999500149; US 5710145; WO 9718809 . |
| 【4】 Faul, M.M.; Winneroski, L.L. Jr.; Krumrich, C.A. (Eli Lilly and Company); Intermediates and their use to prepare N,N'-bridged bisindolylmaleimides. US 5721272 . |
| 【5】 Rito, C.J.; Mcdonald, J.H. III; Jirousek, M.R.; Winneroski, L.L. Jr.; Heath, W.F. Jr.; Faul, M.M. (Eli Lilly and Company); Improved synthesis of bisindolylmaleimides. EP 0657411; US 5541347 . |
| 【6】 Faul, M.M.; Winneroski, L.L. Jr.; Krumrich, C.A. (Eli Lilly and Company); Intermediates and their use to prepare N,N'-bridged bisindolylmaleimides. EP 0776899 . |
| 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) | 16260 | (R)-(+)-Glycidol; (2R)-Oxiranemethanol; (2R)oxiranylmethanol | 57044-25-4 | C3H6O2 | 详情 | 详情 |
| (II) | 28630 | Triphenylchloromethane; 1-[Chloro(diphenyl)methyl]benzene; Trityl chloride | 76-83-5 | C19H15Cl | 详情 | 详情 |
| (III) | 41006 | (2S)-oxiranylmethyl trityl ether; (2S)-2-[(trityloxy)methyl]oxirane | C22H20O2 | 详情 | 详情 | |
| (IV) | 16524 | bromo(vinyl)magnesium | 1826-67-1 | C2H3BrMg | 详情 | 详情 |
| (V) | 41007 | (2S)-1-(trityloxy)-4-penten-2-ol | C24H24O2 | 详情 | 详情 | |
| (VI) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (VII) | 41008 | 1-[[[(2S)-2-(allyloxy)-4-pentenyl]oxy](diphenyl)methyl]benzene; allyl (1S)-1-[(trityloxy)methyl]-3-butenyl ether | C27H28O2 | 详情 | 详情 | |
| (VIII) | 41009 | (3S)-3-(2-oxoethoxy)-4-(trityloxy)butanal | C25H24O4 | 详情 | 详情 | |
| (IX) | 41010 | (3S)-3-(2-hydroxyethoxy)-4-(trityloxy)-1-butanol | C25H28O4 | 详情 | 详情 | |
| (X) | 41011 | (3S)-3-[2-[(methylsulfonyl)oxy]ethoxy]-4-(trityloxy)butyl methanesulfonate | C27H32O8S2 | 详情 | 详情 | |
| (XI) | 41012 | 3,4-di(1H-indol-3-yl)-1-methyl-1H-pyrrole-2,5-dione | 113963-68-1 | C21H15N3O2 | 详情 | 详情 |
| (XII) | 41016 | (18S)-4-methyl-18-[(trityloxy)methyl]-17-oxa-4,14,21-triazahexacyclo[19.6.1.1(7,14).0(2,6).0(8,13).0(22,27)]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaene-3,5-dione | C46H39N3O4 | 详情 | 详情 | |
| (XIII) | 41017 | (18S)-18-[(trityloxy)methyl]-4,17-dioxa-14,21-diazahexacyclo[19.6.1.1(7,14).0(2,6).0(8,13).0(22,27)]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaene-3,5-dione | C45H36N2O5 | 详情 | 详情 | |
| (XIV) | 41014 | (18S)-18-[(trityloxy)methyl]-17-oxa-4,14,21-triazahexacyclo[19.6.1.1(7,14).0(2,6).0(8,13).0(22,27)]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaene-3,5-dione | C45H37N3O4 | 详情 | 详情 | |
| (XV) | 41013 | (18S)-18-(hydroxymethyl)-17-oxa-4,14,21-triazahexacyclo[19.6.1.1(7,14).0(2,6).0(8,13).0(22,27)]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaene-3,5-dione | C26H23N3O4 | 详情 | 详情 | |
| (XVI) | 41018 | (18S)-18-(bromomethyl)-17-oxa-4,14,21-triazahexacyclo[19.6.1.1(7,14).0(2,6).0(8,13).0(22,27)]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaene-3,5-dione | C26H22BrN3O3 | 详情 | 详情 | |
| (XVII) | 41015 | [(18S)-3,5-dioxo-17-oxa-4,14,21-triazahexacyclo[19.6.1.1(7,14).0(2,6).0(8,13).0(22,27)]nonacosa-1(28),2(6),7(29),8,10,12,22,24,26-nonaen-18-yl]methyl methanesulfonate | C27H25N3O6S | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(II)Treatment of (S)-glycidol (I) with triphenylmethyl chloride (Ph3CCl) in pyridine affords O-triphenylmethylglicydyl ether (II), which is then reduced with LiAlH4 in THF to provide alcohol (III). Hydrogenolysis of (III) over Pd/C in MeOH gives 1,2-propandiol (IV), which is then mesylated by means of methanesulfonyl chloride (MsCl) and Et3N in CH2Cl2 to furnish 1-mesyloxy-2-propanol (V). Treatment of tropane (VI) with a refluxing mixture of dioxane/H2O yields carboxylic acid (VII), which is converted into acid chloride (VIII) by means of phosphorus oxychloride (POCl3). Coupling of alcohol (V) with acid chloride (VIII) and Et3N in CH2Cl2 gives tropane derivative (IX), which is finally converted into the target compound by fluorination with tetrabutylammonium fluoride (TBAF) in THF.
| 【1】 Xing, D.; Keil, R.; Chen, P.; et al.; Synthesis, biodistribution, and primate imaging of fluorine-18 labeled 2 beta-carbo-1'-fluoro-2-propoxy-3beta-(4-chlorophenyl)tropanes. Ligands for the imaging of dopamine transporters by positron emission tomography. J Med Chem 2000, 43, 4, 639. |
| 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) | 19241 | (2S)oxiranylmethanol | 60456-23-7 | C3H6O2 | 详情 | 详情 |
| (II) | 41006 | (2S)-oxiranylmethyl trityl ether; (2S)-2-[(trityloxy)methyl]oxirane | C22H20O2 | 详情 | 详情 | |
| (III) | 44832 | (2R)-1-(trityloxy)-2-propanol | C22H22O2 | 详情 | 详情 | |
| (IV) | 19242 | (2S)-1,2-propanediol | 4254-15-3 | C3H8O2 | 详情 | 详情 |
| (V) | 44833 | (2R)-1-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]-2-propanol | C6H14O2S | 详情 | 详情 | |
| (VI) | 44837 | (1R)-1-methyl-2-[[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]ethyl (1S,2S,3S,5R)-3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | C21H30ClNO3S | 详情 | 详情 | |
| (VII) | 44834 | methyl (1S,2S,3S,5R)-3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate | C16H20ClNO2 | 详情 | 详情 | |
| (VIII) | 44835 | (1S,2S,3S,5R)-3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid | C15H18ClNO2 | 详情 | 详情 | |
| (IX) | 44836 | (1S,2S,3S,5R)-3-(4-chlorophenyl)-8-methyl-8-azabicyclo[3.2.1]octane-2-carbonyl chloride | C15H17Cl2NO | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(IV)Treatment of 3-bromobenzyl bromide (I) with sodium methoxide gives 1-bromo-3-(methoxymethyl)benzene (II). After conversion of aryl bromide (II) into the corresponding Grignard reagent (III), addition to epoxide (IV) in the presence of CuI affords the chiral alcohol (V). Removal of the O-trityl protecting group of (V) under acidic conditions provides diol (VI), which is selectively acylated at the primary hydroxyl group by means of acetyl chloride and 2,4,6-collidine to produce the mono-acetate (VII). After protection of the secondary hydroxyl group of (VII) as the tetrahydropyranyl ether (VIII), alkaline hydrolysis of the acetate ester group leads to the primary alcohol (IX). Subsequent Swern oxidation of alcohol (IX) provides aldehyde (X). Condensation of aldehyde (X) with tetrabromomethane in the presence of triphenylphosphine furnishes the gem-dibromoolefin (XI). This is then converted to the terminal alkyne (XII) by treatment with butyllithium in cold THF.
| 【2】 Ohuchida, S.; Maruyama, T. (Ono Pharmaceutical Co., Ltd.); 5-Thia-omega-substd. phenyl-prostaglandin E derivs., process for producing the same and drugs containing the same as the active ingredient. EP 1097922; JP 2001089444; US 6462081; WO 0003980 . |
| 【1】 Maruyama, T.; et al.; Design and synthesis of a selective EP4-receptor agonist. Part 3: 16-Phenyl-5-thiaPGE1 and 9-beta-halo derivatives with improved stability. Bioorg Med Chem 2002, 10, 6, 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) | 20466 | 1-bromo-3-(bromomethyl)benzene | 823-78-9 | C7H6Br2 | 详情 | 详情 |
| (II) | 56397 | 3-bromobenzyl methyl ether; 1-bromo-3-(methoxymethyl)benzene | C8H9BrO | 详情 | 详情 | |
| (III) | 57226 | bromo[3-(methoxymethyl)phenyl]magnesium | C8H9BrMgO | 详情 | 详情 | |
| (IV) | 41006 | (2S)-oxiranylmethyl trityl ether; (2S)-2-[(trityloxy)methyl]oxirane | C22H20O2 | 详情 | 详情 | |
| (V) | 56398 | (2S)-1-[3-(methoxymethyl)phenyl]-3-(trityloxy)-2-propanol | C30H30O3 | 详情 | 详情 | |
| (VI) | 56399 | (2S)-3-[3-(methoxymethyl)phenyl]-1,2-propanediol | C11H16O3 | 详情 | 详情 | |
| (VII) | 56400 | (2S)-2-hydroxy-3-[3-(methoxymethyl)phenyl]propyl acetate | C13H18O4 | 详情 | 详情 | |
| (VIII) | 56401 | (2S)-3-[3-(methoxymethyl)phenyl]-2-(tetrahydro-2H-pyran-2-yloxy)propyl acetate | C18H26O5 | 详情 | 详情 | |
| (IX) | 56402 | (2S)-3-[3-(methoxymethyl)phenyl]-2-(tetrahydro-2H-pyran-2-yloxy)-1-propanol | C16H24O4 | 详情 | 详情 | |
| (X) | 56403 | (2S)-3-[3-(methoxymethyl)phenyl]-2-(tetrahydro-2H-pyran-2-yloxy)propanal | C16H22O4 | 详情 | 详情 | |
| (XI) | 56404 | (1S)-3,3-dibromo-1-[3-(methoxymethyl)benzyl]-2-propenyl tetrahydro-2H-pyran-2-yl ether; 2-({(1S)-3,3-dibromo-1-[3-(methoxymethyl)benzyl]-2-propenyl}oxy)tetrahydro-2H-pyran | C17H22Br2O3 | 详情 | 详情 | |
| (XII) | 56405 | (1S)-1-[3-(methoxymethyl)benzyl]-2-propynyl tetrahydro-2H-pyran-2-yl ether; 2-({(1S)-1-[3-(methoxymethyl)benzyl]-2-propynyl}oxy)tetrahydro-2H-pyran | C17H22O3 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(III)Bromine displacement in 3-bromobenzyl bromide (I) with sodium methoxide gives the methyl ether (II). Subsequent addition of the Grignard reagent prepared from aryl bromide (II) to (S)-O-trityl glycidol (III) in the presence of CuI affords alcohol (IV). Deprotection of the O-trityl group of (IV) under acidic conditions yields diol (V), which is selectively acetylated at the primary hydroxyl group with acetyl chloride and s-collidine in cold CH2Cl2. The resultant secondary alcohol (VI) is then protected as the tetrahydropyranyl ether (VII) upon treatment with dihydropyran and pyridinium p-toluenesulfonate. After basic hydrolysis of the acetate ester (VII), the liberated primary alcohol (VIII) is oxidized to aldehyde (IX) under Swern conditions. Condensation of aldehyde (IX) with carbon tetrabromide in the presence of triphenylphosphine produces the dibromovinyl adduct (X). Debromination of (X) by means of butyllithium in cold THF furnishes the terminal acetylene (XI).
| 【1】 Maruyama, T.; et al.; Design and synthesis of a selective EP4-receptor agonist. Part 3: 16-Phenyl-5-thiaPGE1 and 9-beta-halo derivatives with improved stability. Bioorg Med Chem 2002, 10, 6, 1743. |
| 【2】 Ohuchida, S.; Maruyama, T. (Ono Pharmaceutical Co., Ltd.); 5-Thia-omega-substd. phenyl-prostaglandin E derivs., process for producing the same and drugs containing the same as the active ingredient. EP 1097922; JP 2001089444; US 6462081; WO 0003980 . |
| 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) | 20466 | 1-bromo-3-(bromomethyl)benzene | 823-78-9 | C7H6Br2 | 详情 | 详情 |
| (II) | 56397 | 3-bromobenzyl methyl ether; 1-bromo-3-(methoxymethyl)benzene | C8H9BrO | 详情 | 详情 | |
| (III) | 41006 | (2S)-oxiranylmethyl trityl ether; (2S)-2-[(trityloxy)methyl]oxirane | C22H20O2 | 详情 | 详情 | |
| (IV) | 56395 | (2R,4R,6S,7R,10R,13S,14R,15S,16S,18S)-13-(acetyloxy)-18-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-3-(3-fluoro-2-pyridinyl)-2-[(triisopropylsilyl)oxy]propanoyl}oxy)-4-[(dimethylamino)methyl]-16-hydroxy-7,19,20,20-tetramethyl-3,5,11-trioxapentacyclo[14.3.1.0~2,6~.0~7,14~.0~10,13~]icosa-1(19),8-dien-15-yl benzoate | C55H78FN3O13Si | 详情 | 详情 | |
| (V) | 56399 | (2S)-3-[3-(methoxymethyl)phenyl]-1,2-propanediol | C11H16O3 | 详情 | 详情 | |
| (VI) | 56400 | (2S)-2-hydroxy-3-[3-(methoxymethyl)phenyl]propyl acetate | C13H18O4 | 详情 | 详情 | |
| (VII) | 56401 | (2S)-3-[3-(methoxymethyl)phenyl]-2-(tetrahydro-2H-pyran-2-yloxy)propyl acetate | C18H26O5 | 详情 | 详情 | |
| (VIII) | 56402 | (2S)-3-[3-(methoxymethyl)phenyl]-2-(tetrahydro-2H-pyran-2-yloxy)-1-propanol | C16H24O4 | 详情 | 详情 | |
| (IX) | 56403 | (2S)-3-[3-(methoxymethyl)phenyl]-2-(tetrahydro-2H-pyran-2-yloxy)propanal | C16H22O4 | 详情 | 详情 | |
| (X) | 56404 | (1S)-3,3-dibromo-1-[3-(methoxymethyl)benzyl]-2-propenyl tetrahydro-2H-pyran-2-yl ether; 2-({(1S)-3,3-dibromo-1-[3-(methoxymethyl)benzyl]-2-propenyl}oxy)tetrahydro-2H-pyran | C17H22Br2O3 | 详情 | 详情 | |
| (XI) | 56405 | (1S)-1-[3-(methoxymethyl)benzyl]-2-propynyl tetrahydro-2H-pyran-2-yl ether; 2-({(1S)-1-[3-(methoxymethyl)benzyl]-2-propynyl}oxy)tetrahydro-2H-pyran | C17H22O3 | 详情 | 详情 |