N¹-SES-N⁶-<<3-(benzyloxy)quinolyl>-2-carbonyl>-(D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone

Base Information

• Chemical Name: N¹-SES-N⁶-<<3-(benzyloxy)quinolyl>-2-carbonyl>-(D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone
• CAS No.: 174311-16-1
• Molecular Formula: C₆₂H₈₉N₁₁O₁₆SSi
• Molecular Weight: 1304.6

Synonyms:N¹-SES-N⁶-<<3-(benzyloxy)quinolyl>-2-carbonyl>-(D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone

Chemical Property of N¹-SES-N⁶-<<3-(benzyloxy)quinolyl>-2-carbonyl>-(D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone

Chemical Property:

Purity/Quality:

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Technology Process of N¹-SES-N⁶-<<3-(benzyloxy)quinolyl>-2-carbonyl>-(D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone

There total 27 articles about N¹-SES-N⁶-<<3-(benzyloxy)quinolyl>-2-carbonyl>-(D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

3-(benzyloxy)quinoline-2-carboxylic acid (110429-24-8) + 2-Trimethylsilanyl-ethanesulfonic acid ((3R,7S,16S,23R,27S,36S)-23-amino-7,27-diisopropyl-8,11,28,31-tetramethyl-2,6,9,12,15,22,26,29,32,35-decaoxo-5,25-dioxa-1,8,11,14,21,28,31,34-octaaza-tricyclo[34.4.0.016,21]tetracont-3-yl)-amide; hydrochloride → N1-SES-N6-<<3-(benzyloxy)quinolyl>-2-carbonyl>-(D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone (174311-16-1)

Guidance literature:

With sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 25 ℃; for 48h;

DOI:10.1021/ja952799y

Reference yield:

t-BuOCO-Gly-Sar-OH (133498-97-2) → N1-SES-N6-<<3-(benzyloxy)quinolyl>-2-carbonyl>-(D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone (174311-16-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 74 percent / Et₃N, DCC, DMAP / CH₂Cl₂ / 24 h / 25 °C

2: 90 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 3 h / 25 °C

3: 50 percent / DMAP, DCC / CH₂Cl₂ / 24 h / 0 °C

4: H₂ / 10percent Pd/C / methanol / 12 h / 25 °C

5: 80 percent / NaHCO₃, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h

6: 97 percent / H₂ / 10percent Pd/C / methanol / 16 h / 760 Torr

7: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C

8: 89 percent / NaHCO₃, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C

9: 33 percent / Bu₄NF / tetrahydrofuran / 24 h / 25 °C

10: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C

11: 63 percent / NaHCO₃, HOBt, EDCl / dimethylformamide / 48 h / 25 °C

With hydrogenchloride; dmap; lithium hydroxide; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja952799y

Reference yield:

(S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (26250-84-0) → N1-SES-N6-<<3-(benzyloxy)quinolyl>-2-carbonyl>-(D-Ser-Pip-Gly-Sar-NMe-Val)2(serine hydroxyl) dilactone (174311-16-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 90 percent / NaHCO₃, Bu₄NI / CH₂Cl₂ / 24 h / 25 °C

2: 100 percent / HCl / ethyl acetate / 0.5 h / 25 °C

3: 85 percent / Et₃N, bis(2-oxo-3-oxazolidinyl)phosphinic chloride / CH₂Cl₂ / 10 h / 0 °C

4: 50 percent / DMAP, DCC / CH₂Cl₂ / 24 h / 0 °C

5: H₂ / 10percent Pd/C / methanol / 12 h / 25 °C

6: 80 percent / NaHCO₃, HOBt, EDCl / dimethylformamide / a) 0 deg C, 2 h, b) 25 deg C, 24 h

7: 97 percent / H₂ / 10percent Pd/C / methanol / 16 h / 760 Torr

8: 100 percent / 3M HCl / ethyl acetate / 0.5 h / 25 °C

9: 89 percent / NaHCO₃, diphenyl phosphorazidate / dimethylformamide / 72 h / 0 °C

10: 33 percent / Bu₄NF / tetrahydrofuran / 24 h / 25 °C

11: 100 percent / 3 M HCl / ethyl acetate / 0.5 h / 25 °C

12: 63 percent / NaHCO₃, HOBt, EDCl / dimethylformamide / 48 h / 25 °C

With hydrogenchloride; dmap; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ja952799y

upstream raw materials:

3-(benzyloxy)quinoline-2-carboxylic acid

methyl (2S)-2-[(tert-butoxycarbonyl)(methyl)amino]-3-methylbutanoate

methyl N-methyl-L-valinate hydrochloride

2-trimethylsilanyl-ethanesulfonyl chloride

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