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【结 构 式】 
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【分子编号】12979 【品名】3-Amino-1,2-propanediol；3-aminopropane-1,2-diol 【CA登记号】616-30-8 |
【 分 子 式 】C3H9NO2 【 分 子 量 】91.11 【元素组成】C 39.55% H 9.96% N 15.37% O 35.12% |
合成路线1
该中间体在本合成路线中的序号：(VI)Alternatively, 5-acetamido-2,4,6-triiodoisophthalic acid (I) is alkylated with 1-chloro-3-methoxy-2-propanol (II) to produce (III). After protection of the alcoholic hydroxyl group as the acetate ester (IV), the carboxyl groups are activated as the corresponding acid chloride (V) with SOCl2. Coupling of (V) with 3-amino-1,2-propanediol (VI) then produces the title amide.
| 【1】 Skjoeld, W.; Berg, A.; Preparative liquid chromatography in the field of X-ray contrast agents. J Chromatogr 1986, 366, 299. |
| 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) | 59317 | 5-(acetylamino)-2,4,6-triiodoisophthalic acid | C10H6I3NO5 | 详情 | 详情 | |
| (II) | 34214 | 1-chloro-3-methoxy-2-propanol | 4151-97-7 | C4H9ClO2 | 详情 | 详情 |
| (III) | 59318 | 5-[acetyl(2-hydroxy-3-methoxypropyl)amino]-2,4,6-triiodoisophthalic acid | C14H14I3NO7 | 详情 | 详情 | |
| (IV) | 59319 | 5-{acetyl[2-(acetyloxy)-3-methoxypropyl]amino}-2,4,6-triiodoisophthalic acid | C16H16I3NO8 | 详情 | 详情 | |
| (V) | 59320 | 2-[acetyl-3,5-bis(chlorocarbonyl)-2,4,6-triiodoanilino]-1-(methoxymethyl)ethyl acetate | C16H14Cl2I3NO6 | 详情 | 详情 | |
| (VI) | 12979 | 3-Amino-1,2-propanediol；3-aminopropane-1,2-diol | 616-30-8 | C3H9NO2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)In an alternative method, the tetra-acid chloride (I) derived from O-acetyl-iodixanol is condensed with 3-amino-1,2-propanediol (II) under Schotten-Baumann conditions to afford amide (III). The acetate ester group of (III) is then removed by acidic hydrolysis to furnish the title compound.
| 【1】 Bjoersvik, H.-R.; et al.; N-acylation reactions performed in aqueous reaction medium: Screening and optimising of a synthetic step of a process for iodixanol. Org Process Res Dev 2002, 6, 2, 113. |
| 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) | 59312 | 2-[acetyl-3,5-bis(chlorocarbonyl)-2,4,6-triiodoanilino]-1-{[acetyl-3,5-bis(chlorocarbonyl)-2,4,6-triiodoanilino]methyl}ethyl acetate | C25H14Cl4I6N2O8 | 详情 | 详情 | |
| (II) | 12979 | 3-Amino-1,2-propanediol；3-aminopropane-1,2-diol | 616-30-8 | C3H9NO2 | 详情 | 详情 |
| (III) | 59313 | 2-(acetyl-3,5-bis{[(2,3-dihydroxypropyl)amino]carbonyl}-2,4,6-triiodoanilino)-1-[(acetyl-3,5-bis{[(2,3-dihydroxypropyl)amino]carbonyl}-2,4,6-triiodoanilino)methyl]ethyl acetate | C37H46I6N6O16 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(B)Treatment of 5-amino-2,4,6-triiodo-1,3-benzenedicarboxylic acid (I) with thionyl chloride yields the dichloride (II). Compound (II) is treated with acetoxyacetyl chloride to give compound (III), which is methylated with iodomethane. Condensation with 3-amino-1,2-propanediol of the N-methyl derivative (IV) thus obtained, followed by deacetylation with alkali metal hydroxide, yields iomeprol.
| 【1】 Felder, E.; Musu, C.; Fumagalli, L.; Uggeri, F. (Bracco SpA); Preparation of 5-acylamino-2,4,6-triiodo- or tribromo-benzoic acid derivs.. WO 8809328 . |
| 【2】 Davies, A.; Felder, E.; Tirone, P.; IOMEPROL < Rec INN; BAN; USAN >. Drugs Fut 1990, 15, 11, 1074. |
| 【3】 Musu, C.; Felder, E.; Fumagalli, L.; Piva, R.; Uggeri, F.; Smiles rearrangement, a new synthetic pathway to the synthesis of 5-(hydroxyacyl)-amino-2,4,6-triiodoisophthalamides. Invest Radiol 1990, 25, Suppl. 1, S100-1. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 12979 | 3-Amino-1,2-propanediol；3-aminopropane-1,2-diol | 616-30-8 | C3H9NO2 | 详情 | 详情 |
| (A) | 16601 | ethyl chloroacetate; ethyl 2-chloroacetate | 105-39-5 | C4H7ClO2 | 详情 | 详情 |
| (I) | 22006 | 5-amino-2,4,6-triiodoisophthalic acid | 35453-19-1 | C8H4I3NO4 | 详情 | 详情 |
| (II) | 31194 | 5-amino-2,4,6-triiodoisophthaloyl dichloride | 37441-29-5 | C8H2Cl2I3NO2 | 详情 | 详情 |
| (III) | 31195 | 2-[3,5-bis(chlorocarbonyl)-2,4,6-triiodoanilino]-2-oxoethyl acetate | C12H6Cl2I3NO5 | 详情 | 详情 | |
| (IV) | 31196 | 2-[3,5-bis(chlorocarbonyl)-2,4,6-triiodomethylanilino]-2-oxoethyl acetate | C13H8Cl2I3NO5 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(B)5-Hydroxy-1,3-benzenedicarboxylic acid dimethyl ester (I) is treated with 3-amino-1,2-propanediol to give the corresponding bisamide (II), which is then iodinated with iodine monochloride. The reaction of the triiodinated compound thus obtained (III) with sodium methoxide and chloroacetic acid ethyl ester yields N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[2-ethoxy-2-oxoethoxy]-1,3-benzenedicarboxamide (IV), which is treated with methylamine to give the 5-[2-(methylamino)-2-oxoethoxy] derivative (V). Iomeprol is obtained through a Smiles-type intramolecular rearrangement of (V) in aqueous alkaline medium.
| 【1】 Felder, E.; Pitre, D. (Bracco SpA); Derivs. of 2,4,6-triiodo-isophthalic acid, processes for their synthesis and x-ray contrasting materials containing these. EP 0026281; US 4352788 . |
| 【2】 Davies, A.; Felder, E.; Tirone, P.; IOMEPROL < Rec INN; BAN; USAN >. Drugs Fut 1990, 15, 11, 1074. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (B) | 12979 | 3-Amino-1,2-propanediol；3-aminopropane-1,2-diol | 616-30-8 | C3H9NO2 | 详情 | 详情 |
| (A) | 16601 | ethyl chloroacetate; ethyl 2-chloroacetate | 105-39-5 | C4H7ClO2 | 详情 | 详情 |
| (I) | 31197 | dimethyl 5-hydroxyisophthalate | 13036-02-7 | C10H10O5 | 详情 | 详情 |
| (II) | 31198 | N(1),N(3)-bis(2,3-dihydroxypropyl)-5-hydroxyisophthalamide | C14H20N2O7 | 详情 | 详情 | |
| (III) | 31199 | N(1),N(3)-bis(2,3-dihydroxypropyl)-5-hydroxy-2,4,6-triiodoisophthalamide | C14H17I3N2O7 | 详情 | 详情 | |
| (IV) | 31200 | ethyl 2-(3,5-bis[[(2,3-dihydroxypropyl)amino]carbonyl]-2,4,6-triiodophenoxy)acetate | C18H23I3N2O9 | 详情 | 详情 | |
| (V) | 31201 | N(1),N(3)-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-5-[2-(methylamino)-2-oxoethoxy]isophthalamide | C17H22I3N3O8 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(III)Chlorination of 5-amino-2,4,6-triiodoisophthalic acid (I) with SOCl2 in EtOAc or toluene affords acid chloride (II). Yields have been improved with the addition of benzyltriethylammonium chloride as a catalyst. Acid chloride (II) is then condensed with 3-amino-1,2-propanediol (III) to produce diamide (IV). Compound (IV) is converted to the tetraacetate ester (V) employing acetic anhydride in pyridine. Subsequent acylation of the amino group of (V) with acetoxyacetyl chloride (VI) gives amide (VII). After saponification of the ester groups of (VII), the resultant hydroxy acetamide (VIII) is alkylated by 2-chloroethanol (IX) to furnish the title compound. Alternatively, amide (VIII) is alkylated by bromoethyl acetate (X), producing (XI). Hexa-ester (XI) is finally hydrolyzed with aqueous sulfuric acid. An improved procedure for this final hydrolysis step uses 1,1,2-trichloroethane as co-solvent.
| 【1】 Lin, Y. (Mallinckrodt Medical Inc.); Cpds. suitable for X-ray visualisation methods. EP 0083964; US 4396598 . |
| 【2】 Dunn, T.J.; White, D.H.; Kneller, M.T.; Jones, M.M.; Doran, N.O. III; Bailey, A.R. (Mallinckrodt Medical Inc.); Process for producing ioversol. WO 9727172 . |
| 【3】 Kneller, M.T.; Bailey, A.R.; Sathe, S.S.; Spears, A.T.; Wisneski, R.C. (Mallinckrodt Medical Inc.); Improved synthesis of ioversol. WO 9323365 . |
| 【4】 Villa, M.; Castaldi, G.; Pozzoli, C.; Russo, L. (Zambon Group SpA); Process for the preparation of 5-amino-2,4,6-triiodoisophthalic acid dichloride by chlorination with thionyl chloride in the presence of a catalyst. WO 9636590 . |
| 【5】 Lin, Y.; Dean, R.T.; Kneller, M.; Wallace, R.A.; McCarthy, W.Z.; White, D.H. (Mallinckrodt Medical Inc.); Process for production of ioversol. WO 9111431 . |
| 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) | 22006 | 5-amino-2,4,6-triiodoisophthalic acid | 35453-19-1 | C8H4I3NO4 | 详情 | 详情 |
| (II) | 31194 | 5-amino-2,4,6-triiodoisophthaloyl dichloride | 37441-29-5 | C8H2Cl2I3NO2 | 详情 | 详情 |
| (III) | 12979 | 3-Amino-1,2-propanediol；3-aminopropane-1,2-diol | 616-30-8 | C3H9NO2 | 详情 | 详情 |
| (IV) | 59316 | 5-amino-N~1~,N~3~-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide | C14H18I3N3O6 | 详情 | 详情 | |
| (V) | 59322 | 2-(acetyloxy)-1-({[3-amino-5-({[2,3-bis(acetyloxy)propyl]amino}carbonyl)-2,4,6-triiodobenzoyl]amino}methyl)ethyl acetate | C22H26I3N3O10 | 详情 | 详情 | |
| (VI) | 10456 | Acetoxiacetil chloride; 2-chloro-2-oxoethyl acetate | 13831-31-7 | C4H5ClO3 | 详情 | 详情 |
| (VII) | 59323 | 2-(acetyloxy)-1-({[3-{[2-(acetyloxy)acetyl]amino}-5-({[2,3-bis(acetyloxy)propyl]amino}carbonyl)-2,4,6-triiodobenzoyl]amino}methyl)ethyl acetate | C26H30I3N3O13 | 详情 | 详情 | |
| (VIII) | 59324 | N~1~,N~3~-bis(2,3-dihydroxypropyl)-5-(glycoloylamino)-2,4,6-triiodoisophthalamide | C16H20I3N3O8 | 详情 | 详情 | |
| (IX) | 33463 | 2-bromoethyl acetate | 927-68-4 | C4H7BrO2 | 详情 | 详情 |
| (X) | 10384 | 2-Chloro-1-ethanol; Ethylene chlorohydrin | 107-07-3 | C2H5ClO | 详情 | 详情 |
| (XI) | 59325 | 2-[[2-(acetyloxy)acetyl]-3,5-bis({[2,3-bis(acetyloxy)propyl]amino}carbonyl)-2,4,6-triiodoanilino]ethyl acetate | C30H36I3N3O15 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(VI)The reaction of 5-acetamido-N-(2-hydroxyethyl)isophthalamic acid (I) with 3-chloropropane-1,2-diol (II) and NaOH gives 5-[N-(2,3-dihydroxypropyl)acetamido]-N-(2-hydroxyethyl)-2,4,6-triiodoisophthalamic acid (III), which is acetylated with hot acetic anhydride to the corresponding triacetate (IV). The reaction of (IV) with hot SOCl2 affords the corresponding acyl chloride (V), which is condensed with 2,3-dihydroxypropylamine (VI) by means of triethylamine in dimethylacetamide to give the diamide (VII). Finally, this compound is deacetylated with NaOH in methanol/water.
| 【1】 Prous, J.; Mealy, M.; Castaner, J.; Ioxilan. Drugs Fut 1995, 20, 1, 16. |
| 【2】 Sovak, M.; Ranganathan, R. (Cook Imaging Corp.); Non-ionic polyol contrast media from ionic contrast media. WO 8700757 . |
| 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) | 12974 | 3-(Acetamido)-5-[[(2-hydroxyethyl)amino]carbonyl]-2,4,6-triiodobenzoic acid | C12H11I3N2O5 | 详情 | 详情 | |
| (II) | 12975 | 3-Chloro-1,2-propanediol; Glycerol alpha-monochlorohydrin | 96-24-2 | C3H7ClO2 | 详情 | 详情 |
| (III) | 12976 | 3-[Acetyl(2,3-dihydroxypropyl)amino]-5-[[(2-hydroxyethyl)amino]carbonyl]-2,4,6-triiodobenzoic acid | C15H17I3N2O7 | 详情 | 详情 | |
| (IV) | 12977 | 3-[Acetyl[2,3-bis(acetoxy)propyl]amino]-5-([[2-(acetoxy)ethyl]amino]carbonyl)-2,4,6-triiodobenzoic acid | C21H23I3N2O10 | 详情 | 详情 | |
| (V) | 12978 | 2-[acetyl-3-([[2-(acetoxy)ethyl]amino]carbonyl)-5-(chlorocarbonyl)-2,4,6-triiodoanilino]-1-[(acetoxy)methyl]ethyl acetate | C21H22ClI3N2O9 | 详情 | 详情 | |
| (VI) | 12979 | 3-Amino-1,2-propanediol；3-aminopropane-1,2-diol | 616-30-8 | C3H9NO2 | 详情 | 详情 |
| (VII) | 12980 | 2-(acetyl-3-([[2-(acetoxy)ethyl]amino]carbonyl)-5-[[(2,3-dihydroxypropyl)amino]carbonyl]-2,4,6-triiodoanilino)-1-[(acetoxy)methyl]ethyl acetate | C24H30I3N3O11 | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(I)In a different method, acetylation of 3-amino-1,2-propanediol (I) yields the amide diol (II). Ketalization of cyclohexanone (III) with diol (II) furnishes the spiro dioxolane (IV). The acetamide function of (IV) is then hydrolyzed to amine (V) employing aqueous hydrazine. Amine (V) is condensed with N,N'-di-(carbobenzoxy)-N''-(trifluoromethylsulfonyl)guanidine (VI) to produce the protected guanidine (VII). The N-carbobenzoxy groups of (VII) are finally removed by hydrogenolysis over Pd/C. Alternatively, amine (V) is condensed with cyanogen bromide to produce the cyanamide (VIII). Then, reaction of cyanamide (VIII) with ammonium chloride in aqueous ammonia furnishes the title guanidine compound
| 【1】 Xian, M.; Li, X.; Tang, X.; Chen, X.; Zheng, Z.; Galligan, J.J.; Kreulen, D.L.; Wang, P.G.; N-Hydroxyl derivatives of guanidine based drugs as enzymatic NO donors. Bioorg Med Chem Lett 2001, 11, 17, 2377. |
| 【2】 Xiao, J.-H.; et al.; Endogenous retinoic acid receptor (RAR)-retinoid X receptor (RXR) heterodimers are the major functional forms regulating retinoid-responsive elements in adult human keratinocytes. Binding of ligands to RAR only is sufficient for RAR.RXR heterodimers to co. J Biol Chem 1995, 270, 7, 3001. |
| 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) | 12979 | 3-Amino-1,2-propanediol；3-aminopropane-1,2-diol | 616-30-8 | C3H9NO2 | 详情 | 详情 |
| (II) | 62352 | N-(2,3-dihydroxypropyl)acetamide | C5H11NO3 | 详情 | 详情 | |
| (III) | 11059 | Cyclohexanone | 108-94-1 | C6H10O | 详情 | 详情 |
| (IV) | 62353 | N-(1,4-dioxaspiro[4.5]dec-2-ylmethyl)acetamide | C11H19NO3 | 详情 | 详情 | |
| (V) | 62351 | 1,4-dioxaspiro[4.5]dec-2-ylmethanamine; 1,4-dioxaspiro[4.5]dec-2-ylmethylamine | C9H17NO2 | 详情 | 详情 | |
| (VI) | 62354 | C18H19N3O4 | 详情 | 详情 | ||
| (VII) | 62356 | benzyl (Z)-{[(benzyloxy)carbonyl]amino}[(1,4-dioxaspiro[4.5]dec-2-ylmethyl)amino]methylidenecarbamate | C26H31N3O6 | 详情 | 详情 | |
| (VIII) | 62355 | 1,4-dioxaspiro[4.5]dec-2-ylmethylcyanamide | C10H16N2O2 | 详情 | 详情 |
合成路线8
该中间体在本合成路线中的序号：(VII)Protection of 3-hydroxy-2-methylpyran-4-one (I) with PhCH2Br in the presence of K2CO3 in acetonitrile at 80 °C or in DMF yields 3-(benzyloxy)-2-methylpyran-4-one (II) , which, after deprotonation with LiHMDS in THF, is condensed with benzaldehyde (III) at –60 °C to afford 3-(benzyloxy)-2-(2-hydroxy-2-phenylethyl) pyran-4-one (IV). Sulfonylation of alcohol (IV) with MsCl and Et3N in THF followed by mesylate elimination by means of DBU in NMP gives alkene (V), which by oxidative cleavage with NaIO4 in the presence of RuCl3, optionally using H2S, in acetonitrile/AcOEt/water, and further oxidation of the obtained aldehyde with NaClO2 or NaClO in the presence of TEMPO, yields the pyrancarboxylic acid (VI). Condensation of the 4-pyranone (VI) with 3-aminopropane-1,2-diol (VII) in EtOH at 80 °C leads to the pyridone (VIII), which is then converted to the methyl ester (IX) using MeI and NaHCO3. Oxidative cleavage of the vicinal diol (IX) with NaIO4 and AcOH or H2SO4 in acetonitrile/water provides the pyridone-1-acetaldehyde hydrate (X), which by cyclization with 3(R)-amino-1-butanol (XI) by means of AcOH in MeOH at 90 °C or diglyme yields the pyrido[1’,2’:4,5]pyrazino[2,1-b][1,3]oxazine derivative (XII). Bromination of compound (XII) with NBS in CH2Cl2 or NMP furnishes the bromopyridone derivative (XIII), which undergoes carbonylation with CO in the presence of 2,4-difluorobenzylamine (XIV) and Pd(PPh3)4/DIEA or Pd(OAc)2/DIEA/DPPB in DMSO at 90 °C to afford carboxamide (XV). Finally, compound (XV) is deprotected by debenzylation with H2 over Pd/C .
The pyrancarboxylic acid (VI) can also be prepared by oxidation of 3-(benzyloxy)-2-methylpyran-4-one (XVI) with SeO2 in bromobenzene at 160 °C to give aldehyde (XVII) and further oxidation with NaClO2 in the presence of NH2SO3H in acetone/H2O .
| 【1】 Johns, B.A., Duan, M., Hakogi, T. (Shionogi & Co., Ltd.; GlaxoSmithKline, Inc.). Processes and intermediates for carbamoylpyridone HIV integrase inhibitors. CN 102245572, EP 2376453, JP 2012511574, KR 2011096574, US 2011263855, WO 2010068262. |
| 【2】 Yoshida, H., Taoda, Y., Johns, B.A. (Shionogi & Co., Ltd.; GlaxoSmithKline, Inc.). Synthesis of carbamoylpyridone HIV integrase inhibitors and intermediates. CN 102245182, EP 2376080, JP 012511573, KR 2011094336, US 2011282055, WO 2010068253. |
| 【3】 Johns, B.A., Kawasuji, T., Taishi, T., Taoda, Y. (Shionogi & Co., Ltd.). Polycyclic carbamoylpyridone derivative having HIV integrase inhibitory activity. EP 1874117, EP 2465580, JP 2008540343, JP 2009079058, US 200931821, US 8129385, US 2012115875, WO 2006116764. |
| 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) | 13671 | Hydroxymethylpyrone; 3-Hydroxy-2-methyl-4H-pyran-4-one；Maltol;3-Hydroxy-2-methyl-4-pyrone | 118-71-8 | C6H6O3 | 详情 | 详情 |
| (II) | 12074 | 3-(Benzyloxy)-2-methyl-4H-pyran-4-one；3-(benzyloxy)-2-methylpyran-4-one | 61049-69-2 | C13H12O3 | 详情 | 详情 |
| (III) | 10498 | Benzaldehyde;Benzoic aldehyde;Phenylmethanal | 100-52-7 | C7H6O | 详情 | 详情 |
| (IV) | 68571 | 3-(benzyloxy)-2-(2-hydroxy-2-phenylethyl)-4H-pyran-4-one | C20H18O4 | 详情 | 详情 | |
| (V) | 68572 | (E)-3-(benzyloxy)-2-styryl-4H-pyran-4-one | C20H16O3 | 详情 | 详情 | |
| (VI) | 68573 | 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid | C13H10O5 | 详情 | 详情 | |
| (VII) | 12979 | 3-Amino-1,2-propanediol；3-aminopropane-1,2-diol | 616-30-8 | C3H9NO2 | 详情 | 详情 |
| (VIII) | 68574 | 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid | C16H17NO6 | 详情 | 详情 | |
| (IX) | 68575 | methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate | C17H19NO6 | 详情 | 详情 | |
| (X) | 68576 | methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate | C16H17NO6 | 详情 | 详情 | |
| (XI) | 68577 | 3(R)-amino-1-butanol;(R)-3-aminobutan-1-ol | 61477-39-2 | C4H11NO | 详情 | 详情 |
| (XII) | 68581 | (4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-6,8-dione | C19H20N2O4 | 详情 | 详情 | |
| (XIII) | 68580 | (4R,12aS)-7-(benzyloxy)-9-bromo-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-6,8-dione | C19H19BrN2O4 | 详情 | 详情 | |
| (XIV) | 68578 | 2,4-difluorobenzylamine | 72235-52-0 | C7H7F2N | 详情 | 详情 |
| (XV) | 68579 | (4R,12aS)-7-(benzyloxy)-N-(2,4-difluorobenzyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide | C27H25F2N3O5 | 详情 | 详情 | |
| (XVI) | 12074 | 3-(Benzyloxy)-2-methyl-4H-pyran-4-one；3-(benzyloxy)-2-methylpyran-4-one | 61049-69-2 | C13H12O3 | 详情 | 详情 |
| (XVII) | 68582 | 3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde | C13H10O4 | 详情 | 详情 |