cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate

Base Information

• Chemical Name: cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate
• CAS No.: 892397-05-6
• Molecular Formula: C₃₈H₅₂N₆O₈
• Molecular Weight: 720.866
• Mol file: 892397-05-6.mol

Synonyms:cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate

Chemical Property of cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate

There total 15 articles about cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate 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: 90.0%

cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] (892397-12-5) + pent-4-enoyl chloride (39716-58-0) → cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate (892397-05-6)

Guidance literature:

With triethylamine; dmap; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ol060677c

Reference yield:

(4R,5R)-2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (267653-10-1) → cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate (892397-05-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaOH / methanol; H₂O / 1.5 h / 20 °C

1.2: 47 percent / DIPEA; diphenylphosphoryl azide; NaHCO₃ / dimethylformamide / 48 h / 20 °C

2.1: H₂ / Pd(OH)2/C / methanol

3.1: NaOH / methanol; H₂O / 2 h / 20 °C

3.2: 80 percent / DIPEA; diphenylphosphoryl azide; NaHCO₃ / dimethylformamide / 48 h / 20 °C

4.1: H₂ / Pd(OH)2/C / methanol / 1.5 h / 760 Torr

5.1: NaOH / methanol; H₂O / 2 h / 20 °C

5.2: 0.589 g / NaHCO₃; diphenylphosphoryl azide / dimethylformamide / 72 h / 0 - 20 °C

6.1: 87 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

7.1: 90 percent / triethylamine / DMAP / CH₂Cl₂ / 2 h / 20 °C

With sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; triethylamine; dmap; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ol060677c

Reference yield:

(4R,5R)-2-((S)-1-Amino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (892397-21-6) → cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)] pent-4-enoate (892397-05-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaOH / methanol; H₂O / 1.5 h / 20 °C

1.2: 47 percent / DIPEA; diphenylphosphoryl azide; NaHCO₃ / dimethylformamide / 48 h / 20 °C

2.1: H₂ / Pd(OH)2/C / methanol

3.1: NaOH / methanol; H₂O / 2 h / 20 °C

3.2: 80 percent / DIPEA; diphenylphosphoryl azide; NaHCO₃ / dimethylformamide / 48 h / 20 °C

4.1: H₂ / Pd(OH)2/C / methanol / 1.5 h / 760 Torr

5.1: NaOH / methanol; H₂O / 2 h / 20 °C

5.2: 0.589 g / NaHCO₃; diphenylphosphoryl azide / dimethylformamide / 72 h / 0 - 20 °C

6.1: 87 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

7.1: 90 percent / triethylamine / DMAP / CH₂Cl₂ / 2 h / 20 °C

With sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; triethylamine; dmap; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1021/ol060677c

upstream raw materials:

cyclo[γ-phenyl-allo-homoThr-D-Thr(oxaz)-Val-D-Thr(oxaz)-Val-D-Thr(oxaz)]

pent-4-enoyl chloride

(4R,5R)-2-((S)-1-Amino-2-methyl-propyl)-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

(2S,3R)-methyl 2-amino-3-benzyl-4-(tert-butyldiphenylsilyloxy)butanoate