(5R,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-8-[2-((E)-styryl)-[1,3]dithian-2-yl]-octanoic acid ethyl ester

Base Information

Chemical Name:(5R,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-8-[2-((E)-styryl)-[1,3]dithian-2-yl]-octanoic acid ethyl ester
CAS No.:406676-10-6
Molecular Formula:C₂₈H₄₄O₅S₂Si
Molecular Weight:552.872
Hs Code.:

Synonyms:(5R,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-8-[2-((E)-styryl)-[1,3]dithian-2-yl]-octanoic acid ethyl ester

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Chemical Property of (5R,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-8-[2-((E)-styryl)-[1,3]dithian-2-yl]-octanoic acid ethyl ester

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Technology Process of (5R,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-8-[2-((E)-styryl)-[1,3]dithian-2-yl]-octanoic acid ethyl ester

There total 5 articles about (5R,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-8-[2-((E)-styryl)-[1,3]dithian-2-yl]-octanoic acid ethyl 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:

: 141-97-9
ethyl acetoacetate

: 406676-09-3
(3S)-(tert-butyldimethylsilyloxyl)-4-(2-styryl-[1,3]dithian-2-yl)-butyraldehyde

: 406676-59-3
(5S,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-8-[2-((E)-styryl)-[1,3]dithian-2-yl]-octanoic acid ethyl ester

: 406676-10-6
(5R,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-8-[2-((E)-styryl)-[1,3]dithian-2-yl]-octanoic acid ethyl ester

Guidance literature:: ethyl acetoacetate; With sodium hydride; In tetrahydrofuran; at 0 ℃;

With n-butyllithium; In tetrahydrofuran; hexane; at -10 ℃;

(3S)-(tert-butyldimethylsilyloxyl)-4-(2-styryl-[1,3]dithian-2-yl)-butyraldehyde; In tetrahydrofuran; hexane; at -50 ℃; for 1h;
DOI:10.1016/S0957-4166(01)00506-7

Reference yield:

: 14371-10-9
(E)-3-phenylpropenal

: 406676-10-6
(5R,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-8-[2-((E)-styryl)-[1,3]dithian-2-yl]-octanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 70 percent / ceric ammonium nitrate / CHCl₃ / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.42 h / -78 °C

2.2: 58 percent / BF₃*Et₂O / tetrahydrofuran / 1 h

3.1: 81 percent / imidazole / CH₂Cl₂ / 20 °C

4.1: 95 percent / aq. CF₃COOH / CHCl₃ / 2 h / 0 °C

5.1: NaH / tetrahydrofuran / 0 °C

5.2: n-BuLi / tetrahydrofuran; hexane / -10 °C

5.3: 250 mg / tetrahydrofuran; hexane / 1 h / -50 °C

With 1H-imidazole; n-butyllithium; ammonium cerium(IV) nitrate; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; chloroform;
DOI:10.1016/S0957-4166(01)00506-7

Reference yield:

: 69178-10-5
2-styryl-1,3-dithiane

: 406676-10-6
(5R,7S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-oxo-8-[2-((E)-styryl)-[1,3]dithian-2-yl]-octanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.42 h / -78 °C

1.2: 58 percent / BF₃*Et₂O / tetrahydrofuran / 1 h

2.1: 81 percent / imidazole / CH₂Cl₂ / 20 °C

3.1: 95 percent / aq. CF₃COOH / CHCl₃ / 2 h / 0 °C

4.1: NaH / tetrahydrofuran / 0 °C

4.2: n-BuLi / tetrahydrofuran; hexane / -10 °C

4.3: 250 mg / tetrahydrofuran; hexane / 1 h / -50 °C

With 1H-imidazole; n-butyllithium; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; chloroform;
DOI:10.1016/S0957-4166(01)00506-7