(2S,3R,4R,5S)-2-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan

Base Information

• Chemical Name: (2S,3R,4R,5S)-2-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan
• CAS No.: 259674-78-7
• Molecular Formula: C₂₆H₄₆O₃Si₂
• Molecular Weight: 462.82
• Mol file: 259674-78-7.mol

Synonyms:(2S,3R,4R,5S)-2-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan

Chemical Property of (2S,3R,4R,5S)-2-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S)-2-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan

There total 5 articles about (2S,3R,4R,5S)-2-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan 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:

(3S,4R,5S)-5-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-tetrahydro-furan-2-ol → (2S,3R,4R,5S)-2-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan (259674-78-7)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃;

DOI:10.1055/s-1999-2993

Reference yield:

(3S,4S,5S)-5-But-3-enyl-3,4-dihydroxy-dihydro-furan-2-one → (2S,3R,4R,5S)-2-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan (259674-78-7)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide

2: CeCl₃ / tetrahydrofuran / -78 °C

3: BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / -78 °C

With 1H-imidazole; triethylsilane; cerium(III) chloride; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Grignard reaction / 3: Hydrogenation;

DOI:10.1055/s-1999-2993

Reference yield:

(3S,4R,5S)-5-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-dihydro-furan-2-one (259674-77-6) → (2S,3R,4R,5S)-2-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan (259674-78-7)

Guidance literature:

Multi-step reaction with 2 steps

1: CeCl₃ / tetrahydrofuran / -78 °C

2: BF₃*Et₂O; Et₃SiH / CH₂Cl₂ / -78 °C

With triethylsilane; cerium(III) chloride; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; 1: Grignard reaction / 2: Hydrogenation;

DOI:10.1055/s-1999-2993

upstream raw materials:

(3S,4R,5S)-5-But-3-enyl-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-dihydro-furan-2-one

(2S,3R,4S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-oct-7-enoic acid benzylamide

Downstream raw materials:

3-[(2S,3R,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan-2-yl]-propionaldehyde

3-[(2S,3R,4R,5S)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan-2-yl]-propionic acid methyl ester