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【结 构 式】

【分子编号】25503

【品名】(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate

【CA登记号】

【 分 子 式 】C12H9NO8

【 分 子 量 】295.2054

【元素组成】C 48.82% H 3.07% N 4.74% O 43.36%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XV)

Finally, compound (XIV) is condensed with the mixed carbonate (XV) by literature prodedures.

1 Hebeisen, P.; et al.; Synthesis, physicochemical and pharmacokinetic properties of water soluble prodrugs of Ro 63-9141/000. 38th Intersci Conf Antimicrob Agents Chemother (Sept 24 1998, San Diego) 1998, Abst F-26.
2 Hubschwerlen, C.; Hebeisen, P.; Specklin, J.-L. (F. Hoffmann-La Roche AG); Derivs. of 3-(2-oxo-[1,3']bipyrrolidinyl-3-ylidenemethyl)-cephems. WO 9965920 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XIV) 25502 (6R,7R)-7-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2(Z)-(hydroxyimino)acetamido]-3-[2-oxo-1-(3(R)-pyrrolidinyl)pyrrolidin-3-ylidenemethyl]-3-cephem-4-carboxylic acid C20H22N8O6S2 详情 详情
(XV) 25503 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate C12H9NO8 详情 详情

合成路线2

该中间体在本合成路线中的序号:(V)

The acylating reagent (V) was prepared as follows. Allylic bromination of 4,5-dimethyl-1,3-dioxolene-2-one (I) with N-bromosuccinimide afforded bromide (II). This was converted to alcohol (IV) via formation of the formate ester (III), followed by acidic hydrolysis. Reaction of (IV) with p-nitrophenyl chloroformate and pyridine furnished carbonate (V). The acylation of pseudomycin B (VI) with carbonate (V) produced a mixture of mono-, di- and triacylated compounds from which the desired tricarbamate was isolated by reverse-phase preparative HPLC.

1 Sun, X.; et al.; Synthesis and evaluation of oxodioxolenylmethyl carbamate prodrugs of pseudomycins. J Med Chem 2001, 44, 16, 2671.
2 Chen, S.H.; Sun, X.D.; Rodriguez, M.J. (Eli Lilly and Company); Pseudomycin prodrugs. WO 0105813 .
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) 31106 4,5-dimethyl-1,3-dioxol-2-one 37830-90-3 C5H6O3 详情 详情
(II) 13462 4-(Bromomethyl)-5-methyl-1,3-dioxol-2-one 80715-22-6 C5H5BrO3 详情 详情
(III) 50467 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl formate C6H6O5 详情 详情
(IV) 50468 4-(hydroxymethyl)-5-methyl-1,3-dioxol-2-one C5H6O4 详情 详情
(V) 25503 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 4-nitrophenyl carbonate C12H9NO8 详情 详情
(VI) 50469 (2S)-2-((3S,6S,12S,15S,18S,21S,24R,27S)-18-(4-aminobutyl)-15,24-bis(2-aminoethyl)-21-(carboxymethyl)-3-[(1S)-2-chloro-1-hydroxyethyl]-9-[(Z)ethylidene]-12-[(1S)-1-hydroxyethyl]-27-[[(3R)-3-hydroxytetradecanoyl]amino]-2,5,8,11,14,17,20,23,26-nonaoxo-1-oxa-4,7,10,13,16,19,22,25-octaazacyclooctacosan-6-yl)-2-hydroxyethanoic acid C51H87ClN12O19 详情 详情
Extended Information