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【结 构 式】

【分子编号】46001

【品名】N-alpha-Fmoc--N-epsilon-Z-L-lysine; Fmoc-Nepsilon-Z-L-lysine; N-epsilon-Z-N-alpha-Fmoc-L-lysine; (2S)-6-[[(benzyloxy)carbonyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]hexanoic acid

【CA登记号】86060-82-4

【 分 子 式 】C29H30N2O6

【 分 子 量 】502.56708

【元素组成】C 69.31% H 6.02% N 5.57% O 19.1%

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:(XII)

3-Iodobenzoic acid (I) was converted to ethyl ester (II) by treatment with DCC and DMAP in ethanol. Subsequent Suzuki coupling of (II) with 2-formylbenzeneboronic acid (III) furnished the biphenyl derivative (IV). Formation of oxime (V) using hydroxylamine hydrochloride, followed by reduction with zinc metal and HOAc, afforded amino ester (VI). Saponification of the ethyl ester (VI) gave amino acid (VII), which was coupled with Fmoc-L-valine (VIII) by means of HBTU to yield amide (IX). This compound was attached to Wang resin using DIPC and DMAP to produce resin (X). Deprotection of the Fmoc group by means of piperidine in DMF then gave the corresponding amino compound (XI). To this were incorporated protected amino acid Fmoc-L-lysine(Z) (XII) followed by a deprotection step with piperidine in DMF, to yield the resin-bound peptide (XIII). (Scheme 29421701a)

1 DeGrado, W.F.; Singh, G.; Reisine, T.; Suich, D.J.; Liapakis, G.; Mousa, S.A.; Template-constrained cyclic peptide analogues of somatostatin: Subtype-selective binding to somatostatin receptors and antiangiogenic activity. Bioorg Med Chem 2000, 8, 9, 2229.
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),(X) 45998 2'-[[((2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-methylbutanoyl)amino]methyl][1,1'-biphenyl]-3-carboxylic acid C34H32N2O5 详情 详情
(I) 45991 3-iodobenzoic acid 618-51-9 C7H5IO2 详情 详情
(II) 45992 ethyl 3-iodobenzoate 58313-23-8 C9H9IO2 详情 详情
(III) 45993 2-formylphenylboronic acid 40138-16-7 C7H7BO3 详情 详情
(IV) 45994 ethyl 2'-formyl[1,1'-biphenyl]-3-carboxylate C16H14O3 详情 详情
(V) 45995 ethyl 2'-[(hydroxyimino)methyl][1,1'-biphenyl]-3-carboxylate C16H15NO3 详情 详情
(VI) 45996 ethyl 2'-(aminomethyl)[1,1'-biphenyl]-3-carboxylate C16H17NO2 详情 详情
(VII) 45997 2'-(aminomethyl)[1,1'-biphenyl]-3-carboxylic acid C14H13NO2 详情 详情
(VIII) 19932 (2S)-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-3-methylbutyric acid C20H21NO4 详情 详情
(XI) 45999 2'-([[(2S)-2-amino-3-methylbutanoyl]amino]methyl)[1,1'-biphenyl]-3-carboxylic acid C19H22N2O3 详情 详情
(XII) 46001 N-alpha-Fmoc--N-epsilon-Z-L-lysine; Fmoc-Nepsilon-Z-L-lysine; N-epsilon-Z-N-alpha-Fmoc-L-lysine; (2S)-6-[[(benzyloxy)carbonyl]amino]-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]hexanoic acid 86060-82-4 C29H30N2O6 详情 详情
(XIII) 46000 2'-[(4S,7S)-7-amino-4-isopropyl-3,6,13-trioxo-15-phenyl-14-oxa-2,5,12-triazapentadec-1-yl][1,1'-biphenyl]-3-carboxylic acid C33H40N4O6 详情 详情
Extended Information