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

Base Information

• Chemical Name: cyclo[Boc-(S)-Thr-(S)-Phe-(S)-Phs-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile]
• CAS No.: 370867-58-6
• Molecular Formula: C₅₄H₇₈N₆O₁₁Si
• Molecular Weight: 1015.33
• Mol file: 370867-58-6.mol

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

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

There total 37 articles about cyclo[Boc-(S)-Thr-(S)-Phe-(S)-Phs-(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: 100.0%

cyclo[Boc-(S)-Thr-(S)-Phe-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile] (848780-52-9) → cyclo[Boc-(S)-Thr-(S)-Phe-(S)-Phs-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile] (370867-58-6)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethyl acetate; at 20 ℃; for 3h; under 760 Torr;

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[Boc-(S)-Thr-(S)-Phe-(S)-Phs-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile] (370867-58-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 82 percent / Ag₂O / diethyl ether / 14 h

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

3.1: 60 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 19 h / 0 - 20 °C

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

5.1: 77 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 15 h / 0 - 20 °C

6.1: 75 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C

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

8.1: HCl / dioxane / 1.5 h / 0 °C

9.1: 84 percent / pentafluorophenyl diphenylphosphinate; N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / 20 °C

10.1: zinc; acetic acid / tetrahydrofuran / 4.5 h

10.2: 77 percent / triethylamine / tetrahydrofuran / 6 h / 0 - 20 °C

11.1: 100 percent / H₂ / Pd(OH)2 / ethyl acetate / 3 h / 20 °C / 760 Torr

With morpholine; 1H-imidazole; hydrogenchloride; lithium hydroxide; diethyl cyanophosphonate; pentafluorophenyl diphenyl-phosphinate; hydrogen; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; silver(l) oxide; zinc; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; ethyl acetate; 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[Boc-(S)-Thr-(S)-Phe-(S)-Phs-(S)-Phe-(S)-N-Me-Tyr(TBS)-(S)-Ile] (370867-58-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: HCl / ethyl acetate / 1 h

2.1: 72 percent / bis(2-oxo-3-oxazolidinyl)phosphinic chloride; triethylamine / CH₂Cl₂ / 15 h / 4 °C

3.1: 100 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 0 °C

4.1: HCl / dioxane / 0.5 h

5.1: 60 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 19 h / 0 - 20 °C

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

7.1: 77 percent / diethyl phosphorocyanidate; triethylamine / dimethylformamide / 15 h / 0 - 20 °C

8.1: 75 percent / imidazole / dimethylformamide / 13 h / 0 - 20 °C

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

10.1: HCl / dioxane / 1.5 h / 0 °C

11.1: 84 percent / pentafluorophenyl diphenylphosphinate; N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / 20 °C

12.1: zinc; acetic acid / tetrahydrofuran / 4.5 h

12.2: 77 percent / triethylamine / tetrahydrofuran / 6 h / 0 - 20 °C

13.1: 100 percent / H₂ / Pd(OH)2 / ethyl acetate / 3 h / 20 °C / 760 Torr

With morpholine; 1H-imidazole; hydrogenchloride; lithium hydroxide; diethyl cyanophosphonate; pentafluorophenyl diphenyl-phosphinate; tetrabutyl ammonium fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; palladium dihydroxide; 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:

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

N-(tert-butyloxycarbonyl)-L-isoleucine

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Tyr-OH

Downstream raw materials:

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

C₇₂H₁₀₁N₆O₁₅PSi₂