Phosphoric acid (2S,3R,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,2-dimethyl-propionyl)-5-phenyl-tetrahydro-furan-3-yl ester diethyl ester

Base Information

• Chemical Name: Phosphoric acid (2S,3R,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,2-dimethyl-propionyl)-5-phenyl-tetrahydro-furan-3-yl ester diethyl ester
• CAS No.: 191794-96-4
• Molecular Formula: C₂₆H₄₅O₇PSi
• Molecular Weight: 528.698
• Mol file: 191794-96-4.mol

Synonyms:Phosphoric acid (2S,3R,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,2-dimethyl-propionyl)-5-phenyl-tetrahydro-furan-3-yl ester diethyl ester

Chemical Property of Phosphoric acid (2S,3R,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,2-dimethyl-propionyl)-5-phenyl-tetrahydro-furan-3-yl ester diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphoric acid (2S,3R,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,2-dimethyl-propionyl)-5-phenyl-tetrahydro-furan-3-yl ester diethyl ester

There total 11 articles about Phosphoric acid (2S,3R,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,2-dimethyl-propionyl)-5-phenyl-tetrahydro-furan-3-yl ester diethyl 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: 79.0%

diethyl chlorophosphate (814-49-3) + 1-[(2S,3R,5S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-hydroxy-5-phenyl-tetrahydro-furan-2-yl]-2,2-dimethyl-propan-1-one → Phosphoric acid (2S,3R,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,2-dimethyl-propionyl)-5-phenyl-tetrahydro-furan-3-yl ester diethyl ester (191794-96-4)

Guidance literature:

With lithium diisopropyl amide; at -78 ℃;

DOI:10.1016/0040-4039(96)00782-4

Reference yield:

(2R,3S,5S)-2-Hydroxymethyl-5-phenyl-tetrahydro-furan-3-ol → Phosphoric acid (2S,3R,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,2-dimethyl-propionyl)-5-phenyl-tetrahydro-furan-3-yl ester diethyl ester (191794-96-4)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridine

2: imidazole / dimethylformamide

3: TsOH / CH₂Cl₂

4: 97 percent / CMC, DMSO / pyridine; trifluoroacetic acid

5: 1.) CeCl₃; 2.) periodinane / 1.) THF, -78 deg C; 2.) CH₂Cl₂

6: 92 percent / TBAF / tetrahydrofuran / 0 °C

7: LDA / tetrahydrofuran / -60 °C

8: 65 percent / imidazole / dimethylformamide

9: 1.) Tf₂O, pyridine; 2.) n-Bu₄NNO₃ / 1.) CH₂Cl₂, 0 - 25 deg C; 2.) benzene, 40 deg C

10: 80 percent / Zn, AcOH / CH₂Cl₂ / 0 °C

11: 79 percent / LDA / -78 °C

With pyridine; 1H-imidazole; cerium(III) chloride; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; tetrabutylammonium nitrate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; zinc; lithium diisopropyl amide; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1016/0040-4039(96)00782-4

Reference yield:

1-((2S,3S,5S)-3-Hydroxy-5-phenyl-tetrahydro-furan-2-yl)-2,2-dimethyl-propan-1-one → Phosphoric acid (2S,3R,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-2-(2,2-dimethyl-propionyl)-5-phenyl-tetrahydro-furan-3-yl ester diethyl ester (191794-96-4)

Guidance literature:

Multi-step reaction with 5 steps

1: LDA / tetrahydrofuran / -60 °C

2: 65 percent / imidazole / dimethylformamide

3: 1.) Tf₂O, pyridine; 2.) n-Bu₄NNO₃ / 1.) CH₂Cl₂, 0 - 25 deg C; 2.) benzene, 40 deg C

4: 80 percent / Zn, AcOH / CH₂Cl₂ / 0 °C

5: 79 percent / LDA / -78 °C

With pyridine; 1H-imidazole; trifluoromethylsulfonic anhydride; tetrabutylammonium nitrate; acetic acid; zinc; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(96)00782-4

upstream raw materials:

diethyl chlorophosphate