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【结 构 式】

【分子编号】31377

【品名】S-[(2R,5S,8S)-8-[[(2R)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-yl] O-(4-methylbenzyl) carbonothioate

【CA登记号】

【 分 子 式 】C56H65ClN8O9S

【 分 子 量 】1061.69932

【元素组成】C 63.35% H 6.17% Cl 3.34% N 10.55% O 13.56% S 3.02%

与该中间体有关的原料药合成路线共 3 条

合成路线1

该中间体在本合成路线中的序号:(XII)

Compound (X) was subsequently submitted to further coupling and deprotection cycles with the protected amino acids N-Boc-D-tryptophan (XI) and N-Boc-L-(3-pyridyl)alanine (XIII) to afford the peptide-resins (XII) and (XIV), respectively.

1 Taylor, J.E.; Hocart, S.J.; Murphy, W.A.; Coy, D.H.; Jian, R.; Highly potent cyclic disulfide antagonists of somatostatin. J Med Chem 1999, 42, 11, 1863.
2 Murphy, W.; Coy, D.H.; Morgan, B. (Biomeasure Inc.; Tulane Educational Fund); Somatostatin antagonists. WO 9824807 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(X) 31375 S-[(2R,5S,8S)-8-amino-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-yl] O-(4-methylbenzyl) carbonothioate C45H55ClN6O8S 详情 详情
(XI) 16114 N-alpha-t-BOC-L-tryptophan; (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propionic acid 13139-14-5 C16H20N2O4 详情 详情
(XII) 31377 S-[(2R,5S,8S)-8-[[(2R)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-yl] O-(4-methylbenzyl) carbonothioate C56H65ClN8O9S 详情 详情
(XIII) 31378 (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3-pyridinyl)propionic acid C13H18N2O4 详情 详情
(XIV) 31376 S-[(2R,5S,8S)-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-8-[[(2R)-2-[[(2S)-2-amino-3-(3-pyridinyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec- C64H73ClN10O10S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XI)

The compound was prepared by solid-phase peptide synthesis on a 4-methylbenzhydrylamine-functionalized resin using an automatic peptide synthesizer. Binding of N-Boc-3-(2-naphthyl)-L-alanine (I) to the resin was effected by double coupling, first with the 1,3-diisopropylcarbodiimide active ester, and then a second coupling with the TBTU ester to produce the amino acid-linked resin (II). Deblocking of the Boc group of (II) by treatment with trifluoroacetic acid provided resin (III). The following amino acids were then coupled and deprotected successively to (III) by the same procedure: N-Boc-S-(4-methylbenzyloxycarbonyl)-L-cysteine (IV), N-Boc-L-tert-leucine (VI), N(alpha)-Boc-N(epsilon)-(2-chlorobenzyloxycarbonyl)-L-lysine (VIII) and N-Boc-D-tryptophan (X) yielding the peptide resins (V), (VII), (IX) and (XI), respectively.

1 Rossowski, W.J.; Cheng, B.-L.; Jiang, N.-Y.; Coy, D.-H.; Examination of somatostatin involvement in the inhibitory action of GIP, GLP-1, amylin and adrenomedullin on gastric acid release using a new SRIF antagonist analogue. Br J Pharmacol 1998, 125, 1081.
2 Taylor, J.E.; Hocart, S.J.; Murphy, W.A.; Coy, D.H.; Jian, R.; Highly potent cyclic disulfide antagonists of somatostatin. J Med Chem 1999, 42, 11, 1863.
3 Murphy, W.; Coy, D.H.; Morgan, B. (Biomeasure Inc.; Tulane Educational Fund); Somatostatin antagonists. WO 9824807 .
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) 15061 (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-naphthyl)propionic acid; N-T-BOC-L-3-(2-NAPHTHYL)ALANINE 58438-04-3 C18H21NO4 详情 详情
(II) 31369 tert-butyl (1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethylcarbamate C18H22N2O3 详情 详情
(III) 31370 (2S)-2-amino-3-(2-naphthyl)propanamide C13H14N2O 详情 详情
(IV) 31371 (2R)-2-[(tert-butoxycarbonyl)amino]-3-([[(4-methylbenzyl)oxy]carbonyl]sulfanyl)propionic acid C17H23NO6S 详情 详情
(V) 31372 S-((2R)-2-amino-3-[[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]-3-oxopropyl) O-(4-methylbenzyl) carbonothioate C25H27N3O4S 详情 详情
(VI) 22251 (2S)-2-[(tert-butoxycarbonyl)amino]-3,3-dimethylbutyric acid;2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoic acid;N-(tert-butoxycarbonyl)-3-methyl-L-valine 62965-35-9 C11H21NO4 详情 详情
(VII) 31373 S-((2R)-2-[[(2S)-2-amino-3,3-dimethylbutanoyl]amino]-3-[[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]-3-oxopropyl) O-(4-methylbenzyl) carbonothioate C31H38N4O5S 详情 详情
(VIII) 31374 (2S)-2-[(tert-butoxycarbonyl)amino]-6-([[(2-chlorobenzyl)oxy]carbonyl]amino)hexanoic acid C19H27ClN2O6 详情 详情
(IX) 31375 S-[(2R,5S,8S)-8-amino-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-yl] O-(4-methylbenzyl) carbonothioate C45H55ClN6O8S 详情 详情
(X) 16114 N-alpha-t-BOC-L-tryptophan; (2S)-2-[(tert-butoxycarbonyl)amino]-3-(1H-indol-3-yl)propionic acid 13139-14-5 C16H20N2O4 详情 详情
(XI) 31377 S-[(2R,5S,8S)-8-[[(2R)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-yl] O-(4-methylbenzyl) carbonothioate C56H65ClN8O9S 详情 详情

合成路线3

该中间体在本合成路线中的序号:(XI)

The coupling and deprotection cycles was continued with N-Boc-L-(3-pyridyl)alanine (XII), N-Boc-S-(4-methylbenzyloxy-carbonyl)-D-cysteine (IV), and N-Boc-L-4-fluorophenylalanine (XV), yielding the peptide resins (XIII), (XIV) and (XVI), respectively.

1 Taylor, J.E.; Hocart, S.J.; Murphy, W.A.; Coy, D.H.; Jian, R.; Highly potent cyclic disulfide antagonists of somatostatin. J Med Chem 1999, 42, 11, 1863.
2 Rossowski, W.J.; Cheng, B.-L.; Jiang, N.-Y.; Coy, D.-H.; Examination of somatostatin involvement in the inhibitory action of GIP, GLP-1, amylin and adrenomedullin on gastric acid release using a new SRIF antagonist analogue. Br J Pharmacol 1998, 125, 1081.
3 Murphy, W.; Coy, D.H.; Morgan, B. (Biomeasure Inc.; Tulane Educational Fund); Somatostatin antagonists. WO 9824807 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 31371 (2R)-2-[(tert-butoxycarbonyl)amino]-3-([[(4-methylbenzyl)oxy]carbonyl]sulfanyl)propionic acid C17H23NO6S 详情 详情
(XI) 31377 S-[(2R,5S,8S)-8-[[(2R)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec-1-yl] O-(4-methylbenzyl) carbonothioate C56H65ClN8O9S 详情 详情
(XII) 34944 (2S)-2-[(tert-butoxycarbonyl)(3-pyridinyl)amino]propionic acid C13H18N2O4 详情 详情
(XIII) 31376 S-[(2R,5S,8S)-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-8-[[(2R)-2-[[(2S)-2-amino-3-(3-pyridinyl)propanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-(tert-butyl)-16-(2-chlorophenyl)-4,7,14-trioxo-15-oxa-3,6,13-triazahexadec- C64H73ClN10O10S 详情 详情
(XIV) 31379 S-[(2R,5S,8S,11R,14S,17S)-17-amino-2-([[(1S)-2-amino-1-(2-naphthylmethyl)-2-oxoethyl]amino]carbonyl)-5-(tert-butyl)-8-[4-([[(2-chlorobenzyl)oxy]carbonyl]amino)butyl]-11-(1H-indol-3-ylmethyl)-22-(4-methylphenyl)-4,7,10,13,16,20-hexaoxo-14-(3-pyridiny C76H86ClN11O13S2 详情 详情
(XV) 25929 (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-fluorophenyl)propionic acid C14H18FNO4 详情 详情
(XVI) 34945   C90H102ClFN12O16S2 详情 详情
Extended Information