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【结 构 式】 
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【分子编号】36106 【品名】(5S,10R,13S,16R)-5-[(4R)-4-[(tert-butoxycarbonyl)amino]-5-[2-(tert-butoxycarbonyl)hydrazino]-5-oxopentyl]-10-carboxy-16-hydroxy-13-methyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid 【CA登记号】 |
【 分 子 式 】C30H51N7O14 【 分 子 量 】733.77372 【元素组成】C 49.11% H 7.01% N 13.36% O 30.53% |
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：(XIII)Hydrogenolysis of (XI) with H2 over Pd/C in methanol-acetic acid eliminates the benzyl group giving (XII), which is treated with K2CO3 to eliminate the acetyl group affording (XIII). Treatment of (XIII) with trifluoroacetic acid eliminates the tert-butoxy groups giving FK-156 hydrazide (XIV), which is finally oxidized and hydrolyzed with sodium periodate and H2SO4.
| 【1】 Hemmi, K.; Nakaguchi, O.; Hashimoto, M.; Taleno, H.; Kitaura, Y.; Okada, S.; An efficient method for selective amino acid protection of meso-2,2'-diaminocarboxylic acid: An improved synthesis of FK-156. Tetrahedron Lett 1982, 23, 6, 693-696. |
| 【2】 Okahara, M.; Nakahara, K.; Gotoh, T.; Hashimoto, M..; Kino, T.; Aoki, H.; Imanaka, H.; Kohsaka, M.; Nishiura, T.; Kuroda, Y.; Studies on a new immunoactive peptide, FK-156. II. Fermentation, extraction and chemical and biological charaterization. J Antibiot 1982, 35, 10, 1286-92. |
| 【3】 Gotoh, T.; Imoraka, H.; Nakahara, K.; Tanaka, H.; Uchida, I.; Kawai, Y.; Studies on a new immunoactive peptide, FK-156. III. Structure elucidation. J Antibiot 1982, 35, 10, 1293-99. |
| 【4】 Imanaka, H.; Nakahaa, K.; Gotoh, T.; Aoki, H.; Iwami, M.; Studies on a new immunoactive peptide, FK-156. I. Taxonomy of the producing strains. J Antibiot 1982, 35, 10, 1280-85. |
| 【5】 Okada, S.; Hemmi, K.; Takano, H.; Hashimoto, M.; Nakaguchi, O.; Kitaura, Y.; Aratani, M.; Miyazaki, Y.; Studies of a new immunoactive peptide, FK-156. IV. Synthesis od FK-156 and its geometric isomer. J Antibiot 1982, 35, 10, 1300-11. |
| 【6】 Kitaura, Y.; Nakaguchi, O.; Hemmi, K. (Fujisawa Pharmaceutical Co., Ltd.); New lactyl tetrapeptide, processes for preparation thereof and pharmaceutical compsns. containing it. EP 0011283 . |
| 【7】 Kitaura, Y.; Nakaguchi, O.; Hemmi, K.; Aratani, M.; Takeno, H.; Okada, S.; Tanaka, H.; Hashimoto, M. (Fujisawa Pharmaceutical Co., Ltd.); New peptides, processes for their preparation and pharmaceutical compsns. containing them. EP 0027260 . |
| 【8】 Arya, V.P.; Blancafort, P.; Castaner, J.; Serradell, M.N.; FK-156. Drugs Fut 1983, 8, 8, 667. |
| 【9】 Hemmi, K.; Takeno, H.; Okada, S.; Nakaguchi, O.; Kitaura, Y.; Hashimoto, M.; Total synthesis of FK-156 isolated from a Streptomyces as an immunostimulating peptide: Application of a novel copper chelate amino protection. J Am Chem Soc 1981, 103, 7026. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XI) | 36104 | (4R,7S,10R,15S)-10-[(benzyloxy)carbonyl]-15-[(4R)-4-[(tert-butoxycarbonyl)amino]-5-[2-(tert-butoxycarbonyl)hydrazino]-5-oxopentyl]-4,7-dimethyl-2,5,8,13,16-pentaoxo-3-oxa-6,9,14,17-tetraazanonadecan-19-oic acid | C39H59N7O15 | 详情 | 详情 | |
| (XII) | 36105 | (4R,7S,10R,15S)-15-[(4R)-4-[(tert-butoxycarbonyl)amino]-5-[2-(tert-butoxycarbonyl)hydrazino]-5-oxopentyl]-10-carboxy-4,7-dimethyl-2,5,8,13,16-pentaoxo-3-oxa-6,9,14,17-tetraazanonadecan-19-oic acid | C32H53N7O15 | 详情 | 详情 | |
| (XIII) | 36106 | (5S,10R,13S,16R)-5-[(4R)-4-[(tert-butoxycarbonyl)amino]-5-[2-(tert-butoxycarbonyl)hydrazino]-5-oxopentyl]-10-carboxy-16-hydroxy-13-methyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid | C30H51N7O14 | 详情 | 详情 | |
| (XIV) | 36107 | (5S,10R,13S,16R)-5-[(4R)-4-amino-5-hydrazino-5-oxopentyl]-10-carboxy-16-hydroxy-13-methyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid | C20H35N7O10 | 详情 | 详情 |
Extended Information