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【结 构 式】 
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【分子编号】27188 【品名】5-((1S,2S)-2-[(2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-9-amino-20-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-2,11,12,15-tetrahydroxy-6-[(1R)-1-hydroxyethyl]-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-23-yl]-1,2-dihydroxyethyl)-2-hydroxyphenyl hydrogen sulfate 【CA登记号】 |
【 分 子 式 】C35H52N8O20S 【 分 子 量 】936.9058 【元素组成】C 44.87% H 5.59% N 11.96% O 34.15% S 3.42% |
合成路线1
该中间体在本合成路线中的序号：(VI)The cyclization of the benzoic ester (I) with phenylacetylene (II) by means of triethylamine in THF gives the diphenyl isoxazole (III), which is hydrolyzed with NaOH in ethanol/THF yielding 4-[5-(4-pentyloxyphenyl)isoxazol-3-yl]benzoic acid (IV). The activation of (IV) with HOBT and WSC in dichloromethane affords the benzotriazol-1-yl ester (V), which is finally condensed with the cyclic peptide (VI) by means of DMAP in DMF.
| 【1】 Tomishima, M.; et al.; FK463, a novel water-soluble echinocandin lipopeptide: Synthesis and antifungal activity. J Antibiot 1999, 52, 7, 674. |
| 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) | 27186 | methyl 4-[chloro(hydroxyimino)methyl]benzoate | C9H8ClNO3 | 详情 | 详情 | |
| (II) | 19218 | 4-ethynylphenyl pentyl ether; 1-ethynyl-4-(pentyloxy)benzene | C13H16O | 详情 | 详情 | |
| (III) | 19220 | methyl 4-[5-[4-(pentyloxy)phenyl]-3-isoxazolyl]benzoate | C22H23NO4 | 详情 | 详情 | |
| (IV) | 19221 | 4-[5-[4-(pentyloxy)phenyl]-3-isoxazolyl]benzoic acid | C21H21NO4 | 详情 | 详情 | |
| (V) | 27187 | 1-[(4-[5-[4-(pentyloxy)phenyl]-3-isoxazolyl]benzoyl)oxy]-1H-1,2,3-benzotriazole | C27H24N4O4 | 详情 | 详情 | |
| (VI) | 27188 | 5-((1S,2S)-2-[(2R,6S,9S,11R,12R,14aS,15S,16S,20S,23S,25aS)-9-amino-20-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-2,11,12,15-tetrahydroxy-6-[(1R)-1-hydroxyethyl]-16-methyl-5,8,14,19,22,25-hexaoxotetracosahydro-1H-dipyrrolo[2,1-c:2,1-l][1,4,7,10,13,16]hexaazacyclohenicosin-23-yl]-1,2-dihydroxyethyl)-2-hydroxyphenyl hydrogen sulfate | C35H52N8O20S | 详情 | 详情 |