2-Oxazolidinethione, 3-[(2S,3R,4E)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-1-oxo-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-pentenyl]-4-(phenylmeth yl)-, (4S)-

Base Information

• Chemical Name: 2-Oxazolidinethione, 3-[(2S,3R,4E)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-1-oxo-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-pentenyl]-4-(phenylmeth yl)-, (4S)-
• CAS No.: 836671-02-4
• Molecular Formula: C28H44BNO5SSi
• Molecular Weight: 545.624
• Mol file: 836671-02-4.mol

Synonyms:

Chemical Property of 2-Oxazolidinethione, 3-[(2S,3R,4E)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-1-oxo-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-pentenyl]-4-(phenylmeth yl)-, (4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Oxazolidinethione, 3-[(2S,3R,4E)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-1-oxo-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-pentenyl]-4-(phenylmeth yl)-, (4S)-

There total 4 articles about 2-Oxazolidinethione, 3-[(2S,3R,4E)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-1-oxo-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-pentenyl]-4-(phenylmeth yl)-, (4S)- 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: 84.0%

1-(4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pent-4-en-1-one (836671-00-2) + tert-butyldimethylsilyl chloride (18162-48-6) → (E)-(2S,3R)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pent-4-en-1-one (836671-02-4)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 18h;

DOI:10.1016/j.tet.2004.10.088

Reference yield:

trimethyl([[(2E)-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy])silane (167896-47-1) → (E)-(2S,3R)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pent-4-en-1-one (836671-02-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 9.2 g / citric acid / methanol / 0.08 h

2.1: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

3.1: TiCl₄ / CH₂Cl₂ / 0.08 h / 0 °C

3.2: (-)-sparteine / CH₂Cl₂ / 0.33 h / 0 °C

3.3: 57 percent / CH₂Cl₂ / 2 h / -78 - 0 °C

4.1: 84 percent / imidazole / CH₂Cl₂ / 18 h / 0 - 20 °C

With 1H-imidazole; titanium tetrachloride; Dess-Martin periodane; citric acid; In methanol; dichloromethane;

DOI:10.1016/j.tet.2004.10.088

Reference yield:

(2E)-3-(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)prop-2-enal (153725-01-0) → (E)-(2S,3R)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pent-4-en-1-one (836671-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TiCl₄ / CH₂Cl₂ / 0.08 h / 0 °C

1.2: (-)-sparteine / CH₂Cl₂ / 0.33 h / 0 °C

1.3: 57 percent / CH₂Cl₂ / 2 h / -78 - 0 °C

2.1: 84 percent / imidazole / CH₂Cl₂ / 18 h / 0 - 20 °C

With 1H-imidazole; titanium tetrachloride; In dichloromethane;

DOI:10.1016/j.tet.2004.10.088

upstream raw materials:

1-(4-benzyl-2-thioxooxazolidin-3-yl)-3-hydroxy-2-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pent-4-en-1-one

tert-butyldimethylsilyl chloride

trimethyl([[(2E)-3-(tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy])silane

(2E)-3-(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)prop-2-enal

Downstream raw materials:

6,12-dibromo-9-(tert-butyldimethyl-silanyloxy)-2,4,8-trimethyl-15-phenyl-pentadeca-2,4,6,10,12-pentaenoic acid 2-trimethylsilanyl-ethyl ester

[4-bromo-1-(3,3-dibromo-1-methyl-allyl)-7-phenyl-hepta-2,4-dienyloxy]-tert-butyl-dimethyl-silane

6-bromo-3-(tert-butyl-dimethyl-silanoxy)-2-methyl-9-phenyl-nona-4,6-dienal