[2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propan-1-ol

Base Information

• Chemical Name: [2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propan-1-ol
• CAS No.: 374680-97-4
• Molecular Formula: C₂₉H₅₁ClO₅Si₂
• Molecular Weight: 571.345

Synonyms:[2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propan-1-ol

Chemical Property of [2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propan-1-ol

Chemical Property:

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Technology Process of [2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propan-1-ol

There total 6 articles about [2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propan-1-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: 78.0%

[2R,(1E,3R),3R,4R]-3-allyl-4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)-1-butenyl]-tetrahydrofuran (374680-96-3) → [2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propan-1-ol (374680-97-4)

Guidance literature:

[2R,(1E,3R),3R,4R]-3-allyl-4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)-1-butenyl]-tetrahydrofuran; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; for 2.5h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 5 - 20 ℃;

DOI:10.1021/jo048035v

Reference yield:

(3S,4R)-3-allyl-4-hydroxytetrahydrofuran-2-one (374680-92-9) → [2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propan-1-ol (374680-97-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: imidazole / dimethylformamide / 20 °C

2.1: 103 percent / diisobutylaluminum hydride / toluene / 1.5 h / -60 °C

3.1: 98 percent / triethylamine / tetrahydrofuran / 2 h / 5 - 20 °C

4.1: tert-butyllithium / tetrahydrofuran / 0.67 h / -70 - -60 °C

4.2: litium 2-thienylcyanocuprate / tetrahydrofuran / 0.17 h / -60 °C

4.3: 63 percent / trimethylsilyl bromide / tetrahydrofuran; CH₂Cl₂ / 2 h / -60 °C

5.1: 9-BBN / tetrahydrofuran / 2.5 h

5.2: 78 percent / H₂O₂; sodium hydroxide / tetrahydrofuran / 5 - 20 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; tert.-butyl lithium; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo048035v

Reference yield:

(3S,4R)-3-allyl-4-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-ol (374680-94-1) → [2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propan-1-ol (374680-97-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / triethylamine / tetrahydrofuran / 2 h / 5 - 20 °C

2.1: tert-butyllithium / tetrahydrofuran / 0.67 h / -70 - -60 °C

2.2: litium 2-thienylcyanocuprate / tetrahydrofuran / 0.17 h / -60 °C

2.3: 63 percent / trimethylsilyl bromide / tetrahydrofuran; CH₂Cl₂ / 2 h / -60 °C

3.1: 9-BBN / tetrahydrofuran / 2.5 h

3.2: 78 percent / H₂O₂; sodium hydroxide / tetrahydrofuran / 5 - 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; tert.-butyl lithium; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo048035v

upstream raw materials:

[2R,(1E,3R),3R,4R]-3-allyl-4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)-1-butenyl]-tetrahydrofuran

(3S,4R)-3-allyl-4-hydroxytetrahydrofuran-2-one

(3S,4R)-3-allyl-4-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-ol

(3S,4R)-3-allyl-4-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-one

Downstream raw materials:

isopropyl [2R,(1E,3R),3R,(4Z),4R]-7-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}-hept-4-enoate

(Z)-7-{(2R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-chloro-phenoxy)-but-1-enyl]-tetrahydro-furan-3-yl}-hept-4-enoic acid

[2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propionaldehyde

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