(3R,5S)-5-{2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

Base Information

• Chemical Name: (3R,5S)-5-{2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester
• CAS No.: 693790-20-4
• Molecular Formula: C₄₉H₆₁IN₂O₆S₂Si
• Molecular Weight: 993.155
• Mol file: 693790-20-4.mol

Synonyms:(3R,5S)-5-{2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

Chemical Property of (3R,5S)-5-{2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-5-{2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

There total 16 articles about (3R,5S)-5-{2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester 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%

4-Methyl-benzenesulfinic acid [(S)-3-{2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-but-(E)-ylidene]-amide (693790-17-9) + acetic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester (308240-73-5) → (3R,5S)-5-{2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester (693790-20-4)

Guidance literature:

acetic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.833333h;

4-Methyl-benzenesulfinic acid [(S)-3-{2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-but-(E)-ylidene]-amide; In tetrahydrofuran; at -78 ℃; for 0.166667h;

DOI:10.1139/v03-199

Reference yield:

(S)-4-(tert-butyldiphenylsilanyloxy)-3-(4-methoxybenzyloxy)thiobutyramide (693790-08-8) → (3R,5S)-5-{2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester (693790-20-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 73 percent / 2,6-lutidine / CH₂Cl₂ / 14 h / 20 °C

2.1: 87 percent / (CF₃CO)2O; pyridine / CH₂Cl₂ / 0.33 h / -30 °C

3.1: 92 percent / AcOH / tetrahydrofuran; H₂O / 14 h / 20 °C

4.1: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

5.1: 80 percent / dimethylsulfoxide / 5 h / 60 °C

6.1: 85 percent / DIBAK-H / toluene / 3 h / 0 °C

7.1: 64 percent / Ti(OEt)4 / CH₂Cl₂ / 4 h / Heating

8.1: LiHMDS / tetrahydrofuran / 0.83 h / -78 °C

8.2: 63 percent / tetrahydrofuran / 0.17 h / -78 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) tetraethanolate; DIBAK-H; acetic acid; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene;

DOI:10.1139/v03-199

Reference yield:

(S)-4-(tert-butyldiphenylsilanyloxy)-3-(4-methoxybenzyloxy)butyric acid (693790-33-9) → (3R,5S)-5-{2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester (693790-20-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: ethyl chloroformate; Et₃N / tetrahydrofuran / 0 - 20 °C

1.2: 93 percent / aq. NH₄OH / tetrahydrofuran / 0 - 20 °C

2.1: 99 percent / Lawesson's reagent / diisopropyl ether / 0.5 h / 20 °C

3.1: 73 percent / 2,6-lutidine / CH₂Cl₂ / 14 h / 20 °C

4.1: 87 percent / (CF₃CO)2O; pyridine / CH₂Cl₂ / 0.33 h / -30 °C

5.1: 92 percent / AcOH / tetrahydrofuran; H₂O / 14 h / 20 °C

6.1: 96 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

7.1: 80 percent / dimethylsulfoxide / 5 h / 60 °C

8.1: 85 percent / DIBAK-H / toluene / 3 h / 0 °C

9.1: 64 percent / Ti(OEt)4 / CH₂Cl₂ / 4 h / Heating

10.1: LiHMDS / tetrahydrofuran / 0.83 h / -78 °C

10.2: 63 percent / tetrahydrofuran / 0.17 h / -78 °C

With Lawessons reagent; pyridine; 2,6-dimethylpyridine; titanium(IV) tetraethanolate; DIBAK-H; chloroformic acid ethyl ester; acetic acid; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; di-isopropyl ether; water; dimethyl sulfoxide; toluene;

DOI:10.1139/v03-199

upstream raw materials:

4-Methyl-benzenesulfinic acid [(S)-3-{2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-but-(E)-ylidene]-amide

acetic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester

(S)-4-(tert-butyldiphenylsilanyloxy)-3-(4-methoxybenzyloxy)thiobutyramide

(S)-4-(tert-butyldiphenylsilanyloxy)-3-(4-methoxybenzyloxy)butyramide

Downstream raw materials:

(3R,5S)-3-amino-5-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-2-(4-methoxybenzyloxy)propyl]thiazol-4-yl}hexanoic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester

(3R,5S)-5-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-2-hydroxypropyl]thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethylethoxycarbonylamino)hexanoic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester

(3R,5S)-5-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-2-(4-methoxybenzyloxy)propyl]thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethylethoxycarbonylamino)hexanoic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester