cyclo[Troc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile]

Base Information

• Chemical Name: cyclo[Troc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile]
• CAS No.: 370867-53-1
• Molecular Formula: C₅₉H₇₇Cl₃N₆O₁₁Si
• Molecular Weight: 1180.74
• Mol file: 370867-53-1.mol

Synonyms:cyclo[Troc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile]

Chemical Property of cyclo[Troc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cyclo[Troc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile]

There total 39 articles about cyclo[Troc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile] 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: 84.0%

C59H79Cl3N6O12Si*ClH → cyclo[Troc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile] (370867-53-1)

Guidance literature:

With pentafluorophenyl diphenyl-phosphinate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 17h;

DOI:10.1016/j.tet.2004.12.009

Reference yield:

(S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester (91229-97-9) → cyclo[Troc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile] (370867-53-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / Ag₂O / diethyl ether / 14 h

2: LiOH / tetrahydrofuran; H₂O / 12 h / 20 °C

3: 60 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 19 h / 0 - 20 °C

4: LiOH / tetrahydrofuran; H₂O / 2 h / 0 - 20 °C

5: 77 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 15 h / 0 - 20 °C

6: 75 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C

7: morpholine / (PPh₃)4Pd / tetrahydrofuran / 2 h

8: HCl / dioxane / 1.5 h / 0 °C

9: 84 percent / pentafluorophenyl diphenylphosphinate; N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / 20 °C

With morpholine; 1H-imidazole; hydrogenchloride; lithium hydroxide; diethyl cyanophosphonate; pentafluorophenyl diphenyl-phosphinate; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.12.009

Reference yield:

(S)-methyl-2-((tert-butoxycarbonyl)(methyl)amino)-3-(4-((tert-butyldimethyl-silyl)oxy)phenyl)propanoate (112196-58-4) → cyclo[Troc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile] (370867-53-1)

Guidance literature:

Multi-step reaction with 11 steps

1: HCl / ethyl acetate / 1 h

2: 72 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; triethylamine / CH₂Cl₂ / 15 h / 4 °C

3: 100 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 0 °C

4: HCl / dioxane / 0.5 h

5: 60 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 19 h / 0 - 20 °C

6: LiOH / tetrahydrofuran; H₂O / 2 h / 0 - 20 °C

7: 77 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 15 h / 0 - 20 °C

8: 75 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C

9: morpholine / (PPh₃)4Pd / tetrahydrofuran / 2 h

10: HCl / dioxane / 1.5 h / 0 °C

11: 84 percent / pentafluorophenyl diphenylphosphinate; N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / 20 °C

With morpholine; 1H-imidazole; hydrogenchloride; lithium hydroxide; diethyl cyanophosphonate; pentafluorophenyl diphenyl-phosphinate; tetrabutyl ammonium fluoride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.12.009

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-isoleucine

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Tyr-OH

benzyl bromide

Downstream raw materials:

cyclo[Boc-(S)-Thr-(S)-Phe-(S)-Phs-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile]

phosphoric acid dibenzyl ester 2-benzyloxy-2-[2,15-dibenzyl-8-sec-butyl-21-hydroxy-5-(4-hydroxy-benzyl)-4,11-dimethyl-3,6,9,13,16,22-hexaoxo-10-oxa-1,4,7,14,17-pentaaza-bicyclo[16.3.1]docos-12-ylcarbamoyl]-ethyl ester

phosphoric acid dibenzyl ester 2-benzyloxy-2-[9,15-dibenzyl-3-sec-butyl-6-[4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-7,19-dimethyl-2,5,8,11,14,17-hexaoxo-12-(3-oxo-propyl)-1-oxa-4,7,10,13,16-pentaaza-cyclononadec-18-ylcarbamoyl]-ethyl ester

phosphoric acid dibenzyl ester 2-benzyloxy-2-[9,15-dibenzyl-3-sec-butyl-6-[4-(tert-butyl-dimethyl-silanyloxy)-benzyl]-12-(3-hydroxy-propyl)-7,19-dimethyl-2,5,8,11,14,17-hexaoxo-1-oxa-4,7,10,13,16-pentaaza-cyclononadec-18-ylcarbamoyl]-ethyl ester