(2R,3R,5S)-2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-5-[(E)-(R)-3-(dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl]-2-methoxy-3-methyl-tetrahydro-furan-3-ol

Base Information

• Chemical Name: (2R,3R,5S)-2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-5-[(E)-(R)-3-(dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl]-2-methoxy-3-methyl-tetrahydro-furan-3-ol
• CAS No.: 906671-21-4
• Molecular Formula: C₃₉H₅₆O₄Si₂
• Molecular Weight: 645.042

Synonyms:(2R,3R,5S)-2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-5-[(E)-(R)-3-(dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl]-2-methoxy-3-methyl-tetrahydro-furan-3-ol

Chemical Property of (2R,3R,5S)-2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-5-[(E)-(R)-3-(dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl]-2-methoxy-3-methyl-tetrahydro-furan-3-ol

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Technology Process of (2R,3R,5S)-2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-5-[(E)-(R)-3-(dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl]-2-methoxy-3-methyl-tetrahydro-furan-3-ol

There total 1 articles about (2R,3R,5S)-2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-5-[(E)-(R)-3-(dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl]-2-methoxy-3-methyl-tetrahydro-furan-3-ol 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: 50.0%

(E)-(2S,8R)-1-(tert-Butyl-diphenyl-silanyloxy)-10-(dimethyl-phenyl-silanyl)-2,5,8-trimethyl-5,7-bis-triethylsilanyloxy-undec-9-en-4-one → (2R,5R)-5-[(E)-(R)-3-(Dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl]-2-((S)-3-hydroxy-2-methyl-propyl)-2-methoxy-3-methyl-tetrahydro-furan-3-ol + (2R,3R,5S)-2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-5-[(E)-(R)-3-(dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl]-2-methoxy-3-methyl-tetrahydro-furan-3-ol (906671-21-4)

Guidance literature:

In tetrahydrofuran; methanol; at 0 ℃; for 6h;

DOI:10.1021/ja061918e

Reference yield:

(2R,3R,5S)-2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-5-[(E)-(R)-3-(dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl]-2-methoxy-3-methyl-tetrahydro-furan-3-ol (906671-21-4) → (2R,3R,5S)-2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-5-((E)-(R)-3-iodo-1-methyl-but-2-enyl)-2-methoxy-3-methyl-tetrahydro-furan-3-ol

Guidance literature:

With N-iodo-succinimide; In acetonitrile; at 0 ℃; for 5h;

DOI:10.1021/ja061918e

Reference yield:

(2R,3R,5S)-2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-propyl]-5-[(E)-(R)-3-(dimethyl-phenyl-silanyl)-1-methyl-but-2-enyl]-2-methoxy-3-methyl-tetrahydro-furan-3-ol (906671-21-4) → 4-Methoxy-benzoic acid (2S,3R,5R)-2-{(E)-(R)-5-[(2S,4R,5R)-5-methoxy-5-((E)-(S)-4-methoxycarbonyl-2-methyl-but-3-enyl)-4-methyl-4-trimethylsilanyloxy-tetrahydro-furan-2-yl]-3-methyl-hex-3-enyl}-5-methyl-5-propyl-tetrahydro-furan-3-yl ester

Guidance literature:

Multi-step reaction with 6 steps

1.1: NIS / acetonitrile / 5 h / 0 °C

2.1: TBAF / tetrahydrofuran / 1.5 h / 0 °C

3.1: 83 percent / imidazole / CH₂Cl₂ / 3.5 h / 0 - 20 °C

4.1: DMSO; oxalyl chloride; NEt₃ / CH₂Cl₂ / -78 - 0 °C

5.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

5.2: tetrahydrofuran / -78 - 0 °C

6.1: K₃PO₄; AsPh₃ / (dppf)PdCl₂ / tetrahydrofuran; H₂O; dimethylformamide / 1.5 h

With 1H-imidazole; potassium phosphate; N-iodo-succinimide; oxalyl dichloride; triphenyl-arsane; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 4.1: Swern oxidation / 6.1: Suzuki coupling;

DOI:10.1021/ja061918e

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