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【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%

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:(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
Extended Information