【结 构 式】 |
【分子编号】58829 【品名】(2S)-2-amino-3-(4-methoxy-1H-indol-3-yl)propanoic acid 【CA登记号】 |
【 分 子 式 】C12H14N2O3 【 分 子 量 】234.25484 【元素组成】C 61.53% H 6.02% N 11.96% O 20.49% |
合成路线1
该中间体在本合成路线中的序号:(III)The racemic 4-methoxytryptophan amide (I) is resolved using immobilized Penicillin G acylase, to afford the desired L-aminoacid (III), while leaving unaltered the enantiomeric D-amide (II). After protection of aminoacid (III) as the N-benzyloxycarbonyl derivative (IV), coupling with glycine methyl ester (V) gives dipeptide (VI). Hydrogenolysis of the benzyloxycarbonyl protecting group of (VI) yields amine (VII), which is then coupled with N-Cbz-L-tryptophan (VIII) to produce the protected tripeptide (IX). Hydrogenolysis of (IX) in the presence of Pd/C provides the tripeptide building block (X).
【1】 Ley, S.V.; et al.; Total synthesis of the cyclic heptapeptide argyrin B: A new potent inhibitor of T-cell independent antibody formation. Org Lett 2002, 4, 5, 711. |
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) | 58827 | 4-methoxy-N-(2-phenylacetyl)tryptophan | C20H20N2O4 | 详情 | 详情 | |
(II) | 58828 | (2R)-3-(4-methoxy-1H-indol-3-yl)-2-[(2-phenylacetyl)amino]propanoic acid | C20H20N2O4 | 详情 | 详情 | |
(III) | 58829 | (2S)-2-amino-3-(4-methoxy-1H-indol-3-yl)propanoic acid | C12H14N2O3 | 详情 | 详情 | |
(IV) | 58830 | (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoic acid | C20H20N2O5 | 详情 | 详情 | |
(V) | 17568 | methyl 2-aminoacetate | C3H7NO2 | 详情 | 详情 | |
(VI) | 58831 | methyl 2-{[(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetate | C23H25N3O6 | 详情 | 详情 | |
(VII) | 58832 | methyl 2-{[(2S)-2-amino-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetate | C15H19N3O4 | 详情 | 详情 | |
(VIII) | 18652 | (2S)-2-[[(benzyloxy)carbonyl]amino]-3-(1H-indol-3-yl)propionic acid | 7432-21-5 | C19H18N2O4 | 详情 | 详情 |
(IX) | 58833 | methyl (5S,8S)-5-(1H-indol-3-ylmethyl)-8-[(4-methoxy-1H-indol-3-yl)methyl]-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oate | C34H35N5O7 | 详情 | 详情 | |
(X) | 58834 | methyl 2-{[(2S)-2-{[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino}-3-(4-methoxy-1H-indol-3-yl)propanoyl]amino}acetate | C26H29N5O5 | 详情 | 详情 |