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【结 构 式】 
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【分子编号】56136 【品名】(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-4-({(2R,3R,4R,5R,6R)-3-(acetylamino)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}amino)-2-amino-4-oxobutanoyl]amino}-4-(tert-butoxy)-4-oxobutanoyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-phenylpropanoic acid 【CA登记号】 |
【 分 子 式 】C46H59N7O16 【 分 子 量 】966.01204 【元素组成】C 57.19% H 6.16% N 10.15% O 26.5% |
合成路线1
该中间体在本合成路线中的序号：(XXVI)In an alternative procedure, initial anchoring of N-Fmoc-L-phenylalanine (IX) to the chlorotrityl resin afforded resin (XXI), which was deprotected with piperidine in DMF to provide the phenylalanine-resin (XXII). Sequential coupling and deprotection cycles with N-Fmoc-L-tryptophan (XI), N-Fmoc-L-aspartic acid beta-t-butyl ester (XIII), and N-Fmoc-N’-(tetraacetyl-beta-D-glycosyl)asparragine (XXV) yielded the peptide resins (XXIII), (XXIV) and (XXVI), respectively.
| 【1】 Aimoto, S.; Akaji, K.; Synthesis of MEN11420, a glycosylated bicyclic peptide, by intramolecular double cyclization using a chloroimidazolinium coupling reagent. Tetrahedron 2001, 57, 9, 1749. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX),(XXI) | 19030 | (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-phenylpropionic acid; N-((9H-fluoren-9-ylmethoxy)carbonyl)-phenylalanine | 35661-40-6 | C24H21NO4 | 详情 | 详情 |
| (XI) | 56129 | (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoic acid | C26H22N2O4 | 详情 | 详情 | |
| (XIII) | 22260 | (2S)-4-(tert-butoxy)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-oxobutyric acid | C23H25NO6 | 详情 | 详情 | |
| (XXII) | 13952 | (S)-(-)-Phenylalanine; L-Phenylalanine | 63-91-2 | C9H11NO2 | 详情 | 详情 |
| (XXIII) | 56133 | (2S)-2-{[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino}-3-phenylpropanoic acid | C20H21N3O3 | 详情 | 详情 | |
| (XXIV) | 56134 | (2S)-2-{[(2S)-2-{[(2S)-2-amino-4-(tert-butoxy)-4-oxobutanoyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-phenylpropanoic acid | C28H34N4O6 | 详情 | 详情 | |
| (XXV) | 56135 | (2S)-4-({(2R,3R,4R,5R,6R)-3-(acetylamino)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}amino)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4-oxobutanoic acid | C33H37N3O13 | 详情 | 详情 | |
| (XXVI) | 56136 | (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-4-({(2R,3R,4R,5R,6R)-3-(acetylamino)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}amino)-2-amino-4-oxobutanoyl]amino}-4-(tert-butoxy)-4-oxobutanoyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-phenylpropanoic acid | C46H59N7O16 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XXVI)Another route for the synthesis of intermediate (XVIII) has also been described: To resin (XXVI) was coupled N-Fmoc-L-leucine (IV) to afford resin (XXVII), after Fmoc deprotection with piperidine. Subsequent coupling with the protected diaminopropionic acid (III), followed by a new deprotection with piperidine, gave the resin-bound linear peptide (XXVIII). After trifluoroacetic acid-promoted cleavage from the resin, the resultant side-chain-protected peptide was cyclized to (XVIII)
| 【1】 Aimoto, S.; Akaji, K.; Synthesis of MEN11420, a glycosylated bicyclic peptide, by intramolecular double cyclization using a chloroimidazolinium coupling reagent. Tetrahedron 2001, 57, 9, 1749. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (III) | 56121 | (2S)-3-[(tert-butoxycarbonyl)amino]-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid | C23H26N2O6 | 详情 | 详情 | |
| (XVIII) | 56130 | tert-butyl 2-[(2S,5S,8S,11S,14S,17S)-17-[2-({(2R,3R,4R,5R,6R)-3-(acetylamino)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}amino)-2-oxoethyl]-8-benzyl-11-{[(tert-butoxycarbonyl)amino]methyl}-5-(1H-indol-3-ylmethyl)-14-isobutyl-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexaazacyclooctadecan-2-yl]acetate | C60H82N10O19 | 详情 | 详情 | |
| (XXVI) | 56136 | (2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-4-({(2R,3R,4R,5R,6R)-3-(acetylamino)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}amino)-2-amino-4-oxobutanoyl]amino}-4-(tert-butoxy)-4-oxobutanoyl]amino}-3-(1H-indol-3-yl)propanoyl]amino}-3-phenylpropanoic acid | C46H59N7O16 | 详情 | 详情 | |
| (XXVII) | 56137 | (2S,5S,8S,11S,14S)-11-[2-({(2R,3R,4R,5R,6R)-3-(acetylamino)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}amino)-2-oxoethyl]-14-amino-2-benzyl-8-[2-(tert-butoxy)-2-oxoethyl]-5-(1H-indol-3-ylmethyl)-16-methyl-4,7,10,13-tetraoxo-3,6,9,12-tetraazaheptadecan-1-oic acid | C52H70N8O17 | 详情 | 详情 | |
| (XXVIII) | 56138 | (7S,10S,13S,16S,19S,22S)-13-[2-({(2R,3R,4R,5R,6R)-3-(acetylamino)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl}amino)-2-oxoethyl]-7-amino-22-benzyl-16-[2-(tert-butoxy)-2-oxoethyl]-19-(1H-indol-3-ylmethyl)-10-isobutyl-2,2-dimethyl-4,8,11,14,17,20-hexaoxo-3-oxa-5,9,12,15,18,21-hexaazatricosan-23-oic acid | C60H84N10O20 | 详情 | 详情 |