(R)-4-Benzyl-3-[(Z)-(2S,3R,6R,7S,8S)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-2,4,6-trimethyl-deca-4,9-dienoyl]-oxazolidin-2-one

Base Information

Chemical Name:(R)-4-Benzyl-3-[(Z)-(2S,3R,6R,7S,8S)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-2,4,6-trimethyl-deca-4,9-dienoyl]-oxazolidin-2-one
CAS No.:545339-15-9
Molecular Formula:C₃₀H₄₇NO₆Si
Molecular Weight:545.792
Hs Code.:

Synonyms:(R)-4-Benzyl-3-[(Z)-(2S,3R,6R,7S,8S)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-2,4,6-trimethyl-deca-4,9-dienoyl]-oxazolidin-2-one

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Chemical Property of (R)-4-Benzyl-3-[(Z)-(2S,3R,6R,7S,8S)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-2,4,6-trimethyl-deca-4,9-dienoyl]-oxazolidin-2-one

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Technology Process of (R)-4-Benzyl-3-[(Z)-(2S,3R,6R,7S,8S)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-2,4,6-trimethyl-deca-4,9-dienoyl]-oxazolidin-2-one

There total 16 articles about (R)-4-Benzyl-3-[(Z)-(2S,3R,6R,7S,8S)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-2,4,6-trimethyl-deca-4,9-dienoyl]-oxazolidin-2-one 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: 67.0%

: 101711-78-8,131685-53-5
(3R)-3-propionyl-4-benzyloxazolidin-2-one

: 545339-14-8
(4R,5S,6S,Z)-5-[(tert-butyldimethylsilyl)oxy]-6-methoxy-2,4-dimethylocta-2,7-dienal

: 545339-15-9
(R)-4-Benzyl-3-[(Z)-(2S,3R,6R,7S,8S)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-2,4,6-trimethyl-deca-4,9-dienoyl]-oxazolidin-2-one

Guidance literature:: (3R)-3-propionyl-4-benzyloxazolidin-2-one; (4R,5S,6S,Z)-5-[(tert-butyldimethylsilyl)oxy]-6-methoxy-2,4-dimethylocta-2,7-dienal; With chloro-trimethyl-silane; triethylamine; magnesium chloride; In ethyl acetate; for 36h;

With trifluoroacetic acid; In methanol; for 0.166667h;

Reference yield:

: 72486-93-2
1-methoxy-2-methyl-3-trimethylsiloxy-1,3-pentadiene

: 545339-15-9
(R)-4-Benzyl-3-[(Z)-(2S,3R,6R,7S,8S)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-2,4,6-trimethyl-deca-4,9-dienoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

1.2: 4.31 g / TFA / CH₂Cl₂ / 1 h / 22 °C

2.1: LiBH₄ / methanol; tetrahydrofuran / 0.17 h / -10 °C

3.1: camphorsulfonic acid / tetrahydrofuran / 2 h / Heating

4.1: LiBH₄ / H₂O; tetrahydrofuran / 0.25 h / 22 °C

5.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 22 °C

6.1: 85 percent / aq. AcOH / tetrahydrofuran / 8 h / 22 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / 22 °C

8.1: MgCl₂; Et₃N; TMSCl / ethyl acetate / 36 h / 22 °C

8.2: 219 mg / TFA / methanol / 0.17 h / 22 °C

With 2,6-dimethylpyridine; lithium borohydride; chloro-trimethyl-silane; camphor-10-sulfonic acid; titanium tetrachloride; Dess-Martin periodane; acetic acid; triethylamine; magnesium chloride; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 3.1: Ferrier rerrangement / 7.1: Dess-Martin oxidtion;
DOI:10.1021/ja048779q

Reference yield:

: 261631-97-4
(3S,4R,5R,6S)-3,6-Dimethoxy-octa-1,7-diene-4,5-diol

: 545339-15-9
(R)-4-Benzyl-3-[(Z)-(2S,3R,6R,7S,8S)-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-8-methoxy-2,4,6-trimethyl-deca-4,9-dienoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: Pb(OAc)4; Na₂CO₃ / CH₂Cl₂ / 0 - 22 °C

2.1: TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

2.2: 4.31 g / TFA / CH₂Cl₂ / 1 h / 22 °C

3.1: LiBH₄ / methanol; tetrahydrofuran / 0.17 h / -10 °C

4.1: camphorsulfonic acid / tetrahydrofuran / 2 h / Heating

5.1: LiBH₄ / H₂O; tetrahydrofuran / 0.25 h / 22 °C

6.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 22 °C

7.1: 85 percent / aq. AcOH / tetrahydrofuran / 8 h / 22 °C

8.1: Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / 22 °C

9.1: MgCl₂; Et₃N; TMSCl / ethyl acetate / 36 h / 22 °C

9.2: 219 mg / TFA / methanol / 0.17 h / 22 °C

With 2,6-dimethylpyridine; lead(IV) acetate; lithium borohydride; chloro-trimethyl-silane; camphor-10-sulfonic acid; titanium tetrachloride; sodium carbonate; Dess-Martin periodane; acetic acid; triethylamine; magnesium chloride; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 4.1: Ferrier rerrangement / 8.1: Dess-Martin oxidtion;
DOI:10.1021/ja048779q