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【结 构 式】

【分子编号】62879

【品名】tert-butyl 4-[(4R,7S,10S,13R,16S,19R)-19-{[(2R)-2-amino-3-phenylpropanoyl]amino}-16-benzyl-7-[(1R)-1-hydroxyethyl]-4-({[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]amino}carbonyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-

【CA登记号】

【 分 子 式 】C54H74N10O12S2

【 分 子 量 】1119.37376

【元素组成】C 57.94% H 6.66% N 12.51% O 17.15% S 5.73%

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:(II)

The selective protection of D-Phe1-octreotide peptide (I) with Boc2O gives the monoprotected peptide (II), which is condensed with diethylenetriaminopentaacetic acid (DTPA) dianhydride (III) by means of NaHCO3 in dioxane/water to yield the adduct (IV). The treatment of (IV) with TFA affords the desired DTPA-octreotide derivative (V), which is finally labeled with 111InCl3 in acetic acid or in ammonium citrate to afford the target indium derivative. The starting D-Phe1-octreotide peptide (I) has been obtained by the conventional methods of peptide synthesis using a peptide synthesizer.

1 Wu, Y.-T.; et al.; Direct solid phase synthesis of biologically active peptide alcohols. J Chin Chem Soc (Taipei) 1999, 46, 2, 135.
2 Edwards, W.B.; et al.; Generally applicable, convenient solid-phase synthesis and receptor affinities of octreotide analogs. J Med Chem 1994, 37, 22, 3749.
3 Hsieh, H.-P.; et al.; Direct solid-phase synthesis of octreotide conjugates: Precursors for use as tumor-targeted radiopharmaceuticals. Bioorg Med Chem 1999, 7, 9, 1797.
4 Arano, Y.; et al.; Conventional and high-yield synthesis of DTPA-conjugated peptides: Application of a monoreactive DTPA to DTPA-D-Phe1-octreotide synthesis. Bioconjugate Chem 1997, 8, 3, 442.
5 Bakker, W.H.; et al.; [111In-DTPA-D-Phe1]-octreotide, a potential radiopharmaceutical for imaging of somatostatin receptor-positive tumors: Synthesis, radiolabeling and in vitro validation. Life Sci 1991, 49, 22, 1583.
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) 62878 (4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-19-{[(2R)-2-amino-3-phenylpropanoyl]amino}-16-benzyl-7-[(1R)-1-hydroxyethyl]-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacyclo C49H66N10O10S2 详情 详情
(II) 62879 tert-butyl 4-[(4R,7S,10S,13R,16S,19R)-19-{[(2R)-2-amino-3-phenylpropanoyl]amino}-16-benzyl-7-[(1R)-1-hydroxyethyl]-4-({[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]amino}carbonyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17- C54H74N10O12S2 详情 详情
(III) 49150 Diethylenetriaminepentaacetic acid; N,N-Bis[2-(2,6-dioxomorpholino)ethyl]glycine 23911-26-4 C14H19N3O8 详情 详情
(IV) 62880 2-[{2-[((1R)-1-benzyl-2-{[(4R,7S,10S,13R,16S,19R)-16-benzyl-10-{4-[(tert-butoxycarbonyl)amino]butyl}-7-[(1R)-1-hydroxyethyl]-4-({[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]amino}carbonyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8 C68H93N13O20S2 详情 详情
(V) 62881 (13R)-14-{[(4R,7S,10S,13R,16S,19R)-10-(4-aminobutyl)-16-benzyl-7-[(1R)-1-hydroxyethyl]-4-({[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]amino}carbonyl)-13-(1H-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-19-yl]am C63H87N13O19S2 详情 详情
Extended Information