(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-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)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester
CAS No.:308240-82-6
Molecular Formula:C₄₂H₆₃IN₂O₆S₂Si
Molecular Weight:911.094
Hs Code.:

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

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

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

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

There total 15 articles about (3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-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:

: 308240-73-5
acetic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester

: 4-Methyl-benzenesulfinic acid [(S)-3-{2-[(S)-2-(4-methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-but-(E)-ylidene]-amide

: 308240-82-6
(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

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

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.166667h;
DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

: 276870-05-4
(3S)-3-hydroxy-4-(triisopropylsilyloxy)butyric acid methyl ester

: 308240-82-6
(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

Guidance literature:: Multi-step reaction with 13 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

With Lawessons reagent; pyridine; 2,6-dimethylpyridine; titanium(IV) tetraethanolate; lithium hydroxide; ammonium hydroxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; acetic acid; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; 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;
DOI:10.1016/S0040-4039(00)01241-7

Reference yield:

: 308240-90-6
(+)-(S)-4-tert-Butyldimethylsilyloxy-3-methyl-2-butanone

: 308240-82-6
(3R,5S)-5-{2-[(S)-2-(4-Methoxy-benzyloxy)-3-triisopropylsilanyloxy-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester

Guidance literature:: Multi-step reaction with 9 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

With pyridine; 2,6-dimethylpyridine; titanium(IV) tetraethanolate; diisobutylaluminium hydride; acetic acid; triethylamine; trifluoroacetic anhydride; lithium hexamethyldisilazane; In tetrahydrofuran; 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;
DOI:10.1016/S0040-4039(00)01241-7