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【结 构 式】 
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【分子编号】64692 【品名】ethyl 5-{[tert-butyl(dimethyl)silyl]oxy}-4-oxopentanoate 【CA登记号】 |
【 分 子 式 】C13H26O4Si 【 分 子 量 】274.43254 【元素组成】C 56.9% H 9.55% O 23.32% Si 10.23% |
合成路线1
该中间体在本合成路线中的序号：(VI)The condensation of 13C-labelled methyl phenyl sulfone (I) with 2-(tert-butyldimethylsilyloxy)acetic acid ethyl ester (II) by means of BuLi in THF gives the labelled propanone derivative (III), which is condensed with ethyl 2-bromoacetate (IV) by means of NaH in THF to yield the gamma-oxo ester (V). Desulfurization of (V) by means of Al/Hg in THF/water affords the silylated 5-hydroxy-4-oxopentanoic acid ethyl ester (VI), which is desilylated by means of AcOH in THF/water to provide the free hydroxyester (VII). The condensation of (VII) with phthalimide (VIII) by means of DEAD and PPh3 in toluene gives the phthalimido derivative (IX), which is finally treated with refluxing 6N HCl to provide the target labelled aminolevulinic acid.
| 【1】 Kurumaya, K.; Okazaki, T.; Seido, N.; Akasaka, Y.; Kawajiri, Y.; Kajiwara, M.; Kondo, M.; Facile synthesis of delta-aminolevulinic acid (ALA) regioselectively labeled with 13C and direct observation of enzymatic transformation from ALA to porphobilinogen (PBG). J Label Compd Radiopharm 1989, 27, 2, 217. |
| 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) | 23622 | methyl phenyl sulfone; methyl(dioxo)phenyl-lambda(6)-sulfane | 3112-85-4 | C7H8O2S | 详情 | 详情 |
| (I) | 61635 | methyl phenyl sulfone; methyl(dioxo)phenyl-lambda~6~-sulfane | C7H8O2S | 详情 | 详情 | |
| (II) | 61636 | ethyl 2-{[tert-butyl(dimethyl)silyl]oxy}acetate | C10H22O3Si | 详情 | 详情 | |
| (III) | 61637 | 1-{[tert-butyl(dimethyl)silyl]oxy}-3-(phenylsulfonyl)acetone | C15H24O4SSi | 详情 | 详情 | |
| (III) | 64694 | 1-{[tert-butyl(dimethyl)silyl]oxy}-3-(phenylsulfonyl)acetone | C15H24O4SSi | 详情 | 详情 | |
| (IV) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (V) | 61639 | ethyl 5-{[tert-butyl(dimethyl)silyl]oxy}-4-oxo-3-(phenylsulfonyl)pentanoate | C19H30O6SSi | 详情 | 详情 | |
| (V) | 64691 | ethyl 5-{[tert-butyl(dimethyl)silyl]oxy}-4-oxo-3-(phenylsulfonyl)pentanoate | C19H30O6SSi | 详情 | 详情 | |
| (VI) | 61640 | ethyl 5-{[tert-butyl(dimethyl)silyl]oxy}-4-oxopentanoate | C13H26O4Si | 详情 | 详情 | |
| (VI) | 64692 | ethyl 5-{[tert-butyl(dimethyl)silyl]oxy}-4-oxopentanoate | C13H26O4Si | 详情 | 详情 | |
| (VII) | 61641 | ethyl 5-hydroxy-4-oxopentanoate | C7H12O4 | 详情 | 详情 | |
| (VII) | 64693 | ethyl 5-hydroxy-4-oxopentanoate | C7H12O4 | 详情 | 详情 | |
| (VIII) | 12376 | Phthalimide; 1H-Isoindole-1,3(2H)-dione; Isoindole-1,3-dione;Phthalic dicarboximide;Phenylimide;Isoindole-1,3-dione | 85-41-6 | C8H5NO2 | 详情 | 详情 |
| (IX) | 59167 | ethyl 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoate | C15H15NO5 | 详情 | 详情 | |
| (IX) | 61642 | ethyl 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoate | C15H15NO5 | 详情 | 详情 |