(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

Base Information

Chemical Name:(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
CAS No.:693790-44-2
Molecular Formula:C₃₉H₅₂Cl₃IN₂O₆SSi
Molecular Weight:938.267
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 20 articles about (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 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: 87.0%

: 693790-22-6
(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

: 693790-44-2
(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

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 1.5h;
DOI:10.1139/v03-199

Reference yield:

: 693790-08-8
(S)-4-(tert-butyldiphenylsilanyloxy)-3-(4-methoxybenzyloxy)thiobutyramide

: 693790-44-2
(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

Guidance literature:: Multi-step reaction with 11 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

9.1: 95 percent / TDA / methanol / 4 h / 20 °C

10.1: 86 percent / pyridine / CH₂Cl₂ / 1.5 h / 0 °C

11.1: 87 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) tetraethanolate; DIBAK-H; acetic acid; triethylamine; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene;
DOI:10.1139/v03-199

Reference yield:

: 693790-33-9
(S)-4-(tert-butyldiphenylsilanyloxy)-3-(4-methoxybenzyloxy)butyric acid

: 693790-44-2
(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

Guidance literature:: Multi-step reaction with 13 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

11.1: 95 percent / TDA / methanol / 4 h / 20 °C

12.1: 86 percent / pyridine / CH₂Cl₂ / 1.5 h / 0 °C

13.1: 87 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1.5 h / 0 °C

With Lawessons reagent; pyridine; 2,6-dimethylpyridine; titanium(IV) tetraethanolate; DIBAK-H; chloroformic acid ethyl ester; acetic acid; triethylamine; trifluoroacetic anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; di-isopropyl ether; water; dimethyl sulfoxide; toluene;
DOI:10.1139/v03-199