2,2-Dimethyl-propionic acid (3R,5S)-5-hydroxy-3-(4-methoxy-benzyloxy)-8-trimethylsilanyl-oct-7-ynyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (3R,5S)-5-hydroxy-3-(4-methoxy-benzyloxy)-8-trimethylsilanyl-oct-7-ynyl ester
CAS No.:397886-69-0
Molecular Formula:C₂₄H₃₈O₅Si
Molecular Weight:434.648
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (3R,5S)-5-hydroxy-3-(4-methoxy-benzyloxy)-8-trimethylsilanyl-oct-7-ynyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (3R,5S)-5-hydroxy-3-(4-methoxy-benzyloxy)-8-trimethylsilanyl-oct-7-ynyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (3R,5S)-5-hydroxy-3-(4-methoxy-benzyloxy)-8-trimethylsilanyl-oct-7-ynyl ester

There total 9 articles about 2,2-Dimethyl-propionic acid (3R,5S)-5-hydroxy-3-(4-methoxy-benzyloxy)-8-trimethylsilanyl-oct-7-ynyl 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:

: 1066-54-2
trimethylsilylacetylene

: 397886-52-1
2,2-Dimethyl-propionic acid (R)-3-(4-methoxy-benzyloxy)-4-(R)-oxiranyl-butyl ester

: 397886-69-0
2,2-Dimethyl-propionic acid (3R,5S)-5-hydroxy-3-(4-methoxy-benzyloxy)-8-trimethylsilanyl-oct-7-ynyl ester

Guidance literature:: trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

2,2-Dimethyl-propionic acid (R)-3-(4-methoxy-benzyloxy)-4-(R)-oxiranyl-butyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Further stages.;
DOI:10.1021/ol0102592

Reference yield:

: 87318-96-5
(4S)-4-((2R)-2-hydroxypent-4-enyl)-2,2-dimethyl-1,3-dioxolane

: 397886-69-0
2,2-Dimethyl-propionic acid (3R,5S)-5-hydroxy-3-(4-methoxy-benzyloxy)-8-trimethylsilanyl-oct-7-ynyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 - 20 °C

1.2: 100 percent / dimethylformamide / 20 °C

2.1: 92 percent / HOAc / H₂O; tetrahydrofuran / 8 h / 45 - 50 °C

3.1: 91 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 97 percent / DMAP; pyridine / CH₂Cl₂ / 0 - 20 °C

5.1: 89 percent / K₂CO₃ / methanol / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: BF₃*Et₂O / tetrahydrofuran; hexane / 0.33 h / -78 °C

6.3: tetrahydrofuran; hexane / 1 h / -78 °C

With pyridine; dmap; n-butyllithium; sodium hydride; potassium carbonate; acetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol0102592

Reference yield:

: 3282-30-2
pivaloyl chloride

: 397886-69-0
2,2-Dimethyl-propionic acid (3R,5S)-5-hydroxy-3-(4-methoxy-benzyloxy)-8-trimethylsilanyl-oct-7-ynyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: BF₃*Et₂O / tetrahydrofuran; hexane / 0.33 h / -78 °C

1.3: tetrahydrofuran; hexane / 1 h / -78 °C

With n-butyllithium; In tetrahydrofuran; hexane;
DOI:10.1021/ol0102592