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【结 构 式】

【分子编号】63272

【品名】(2S)-2-[(2-{[(2S)-2-amino-3-methyl-3-(tritylsulfanyl)butanoyl]amino}acetyl)amino]-3-phenylpropanoic acid

【CA登记号】

【 分 子 式 】C35H37N3O4S

【 分 子 量 】595.7626

【元素组成】C 70.56% H 6.26% N 7.05% O 10.74% S 5.38%

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:(VI)

The title compound is prepared by solid-phase peptide synthesis starting from N-Fmoc-L-phenylalanine attached to Wang resin (I). Deprotection of (I) with piperidine in NMP removes the N-Fmoc group, yielding the phenylalanine resin (II). Coupling of (II) with N-trityl glycine (III) in the presence of PyBOP and HOBt, followed by acidic cleavage of the N-trityl group furnishes the dipeptide derivative (IV). To this is assembled N-Fmoc-S-trityl-D-penicillamine (V), followed by deprotection with piperidine in NMP, to produce resin (VI). Subsequent coupling of (VI) with N-Cbz-O-benzyl-L-tyrosine (VII) leads to the protected tetrapeptide (VIII). Removal of the S-trityl protecting group of (VIII) employing trifluoroacetic acid provides thiol (IX).

1 Rew, Y.; Malkmus, S.; Svensson, C.; Yaksh, T.L.; Chung, N.N.; Schiller, P.W.; Cassel, J.A.; DeHaven, R.; Goodman, M.; Synthesis and biological activities of cyclic lanthionine enkephalin analogues: delta-Opioid receptor selective ligands. J Med Chem 2002, 45, 17, 3746.
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) 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
(II) 13952 (S)-(-)-Phenylalanine; L-Phenylalanine 63-91-2 C9H11NO2 详情 详情
(III) 63269 2-(tritylamino)acetic acid C21H19NO2 详情 详情
(IV) 63270 (2S)-2-[(2-aminoacetyl)amino]-3-phenylpropanoic acid C11H14N2O3 详情 详情
(V) 63271 (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-methyl-3-(tritylsulfanyl)butanoic acid C39H35NO4S 详情 详情
(VI) 63272 (2S)-2-[(2-{[(2S)-2-amino-3-methyl-3-(tritylsulfanyl)butanoyl]amino}acetyl)amino]-3-phenylpropanoic acid C35H37N3O4S 详情 详情
(VII) 27842 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-[4-(benzyloxy)phenyl]propionic acid C24H23NO5 详情 详情
(VIII) 63273 (5S,8S,14S)-14-benzyl-5-[4-(benzyloxy)benzyl]-8-[1-methyl-1-(tritylsulfanyl)ethyl]-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazapentadecan-15-oic acid C59H58N4O8S 详情 详情
(IX) 63274 (5S,8S,14S)-14-benzyl-5-[4-(benzyloxy)benzyl]-8-(1-methyl-1-sulfanylethyl)-3,6,9,12-tetraoxo-1-phenyl-2-oxa-4,7,10,13-tetraazapentadecan-15-oic acid C40H44N4O8S 详情 详情
Extended Information