(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

Base Information

• Chemical Name: (3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester
• CAS No.: 308240-95-1
• Molecular Formula: C₄₀H₆₂Cl₃IN₂O₇SSi
• Molecular Weight: 976.356

Synonyms:(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

Chemical Property of (3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

Chemical Property:

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Technology Process of (3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

There total 17 articles about (3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-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: 89.0%

2,2,2-trichloro-1,1-dimethylethoxychloroformate (66270-36-8) + (3R,5S)-3-Amino-5-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester (308240-94-0) → (3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester (308240-95-1)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

(3S)-3-hydroxy-4-(triisopropylsilyloxy)butyric acid methyl ester (276870-05-4) → (3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester (308240-95-1)

Guidance literature:

Multi-step reaction with 15 steps

1: 76 percent / CSA / CH₂Cl₂ / 72 h / 20 °C

2: 90 percent / LiOH / tetrahydrofuran; H₂O / 12 h / 20 °C

3: Et₃N / 20 °C

4: NH₄OH / 0.5 h / 20 °C

5: 99 percent / Lawesson's reagent / tetrahydrofuran / 0.5 h / 20 °C

6: 2,6-lutidene / CH₂Cl₂ / 12 h / 20 °C

7: (CF₃CO)2O; pyridine / CH₂Cl₂ / 0.5 h / -30 °C

8: 92 percent / AcOH / tetrahydrofuran; H₂O / 12 h / 20 °C

9: Et₃N / CH₂Cl₂ / 1 h / 0 °C

10: dimethylsulfoxide / 6 h / 60 °C

11: 85 percent / DIBAL / toluene / 2 h / 0 °C

12: 64 percent / Ti(OEt)4 / CH₂Cl₂ / 4 h / 50 °C

13: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C

14: 95 percent / TFA / methanol / 4 h / 20 °C

15: 89 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With Lawessons reagent; pyridine; 2,6-dimethylpyridine; titanium(IV) tetraethanolate; lithium hydroxide; ammonium hydroxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; acetic acid; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; 1: Alkylation / 2: Hydrolysis / 3: Acylation / 4: amidation / 5: Substitution / 6: Cyclization / 7: Dehydration / 8: Elimination / 9: mesylation / 10: Substitution / 11: Hydrogenation / 12: Condensation / 13: Addition / 14: Hydrolysis / 15: Acylation;

DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

(+)-(S)-4-tert-Butyldimethylsilyloxy-3-methyl-2-butanone (308240-90-6) → (3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester (308240-95-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: LiHMDS / -78 °C

1.2: 86 percent / TMSCl; Br₂

2.1: 2,6-lutidene / CH₂Cl₂ / 12 h / 20 °C

3.1: (CF₃CO)2O; pyridine / CH₂Cl₂ / 0.5 h / -30 °C

4.1: 92 percent / AcOH / tetrahydrofuran; H₂O / 12 h / 20 °C

5.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

6.1: dimethylsulfoxide / 6 h / 60 °C

7.1: 85 percent / DIBAL / toluene / 2 h / 0 °C

8.1: 64 percent / Ti(OEt)4 / CH₂Cl₂ / 4 h / 50 °C

9.1: LiHMDS / tetrahydrofuran / 0.17 h / -78 °C

10.1: 95 percent / TFA / methanol / 4 h / 20 °C

11.1: 89 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) tetraethanolate; diisobutylaluminium hydride; acetic acid; triethylamine; trifluoroacetic acid; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; 1.1: deprotonation / 1.2: Bromination / 2.1: Cyclization / 3.1: Dehydration / 4.1: Elimination / 5.1: mesylation / 6.1: Substitution / 7.1: Hydrogenation / 8.1: Condensation / 9.1: Addition / 10.1: Hydrolysis / 11.1: Acylation;

DOI:10.1016/S0040-4039(00)01241-7

upstream raw materials:

2,2,2-trichloro-1,1-dimethylethoxychloroformate

(3R,5S)-3-Amino-5-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

(3S)-3-hydroxy-4-(triisopropylsilyloxy)butyric acid methyl ester

(+)-(S)-4-tert-Butyldimethylsilyloxy-3-methyl-2-butanone

Downstream raw materials:

(-)-pateamine

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