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【结 构 式】

【分子编号】61637

【品名】1-{[tert-butyl(dimethyl)silyl]oxy}-3-(phenylsulfonyl)acetone

【CA登记号】

【 分 子 式 】C15H24O4SSi

【 分 子 量 】328.50466

【元素组成】C 54.84% H 7.36% O 19.48% S 9.76% Si 8.55%

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:(III)

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
Extended Information