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

Base Information

• Chemical Name: [2R,(1E,3R),3R,4R]-3-allyl-4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)-1-butenyl]-tetrahydrofuran
• CAS No.: 374680-96-3
• Molecular Formula: C₂₉H₄₉ClO₄Si₂
• Molecular Weight: 553.33

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about [2R,(1E,3R),3R,4R]-3-allyl-4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)-1-butenyl]-tetrahydrofuran 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: 63.0%

(E)-1-iodo-4-(3-chlorophenoxy)-3(R)-(tert-butyldimethylsilyloxy)-1-butene (443361-70-4) + (3S,4R)-3-allyl-4-(tert-butyldimethylsilyloxy)-2-trimethylsilyloxytetrahydrofuran (374680-95-2) → [2R,(1E,3R),3R,4R]-3-allyl-4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)-1-butenyl]-tetrahydrofuran (374680-96-3)

Guidance literature:

(E)-1-iodo-4-(3-chlorophenoxy)-3(R)-(tert-butyldimethylsilyloxy)-1-butene; With tert.-butyl lithium; In tetrahydrofuran; at -70 - -60 ℃; for 0.666667h;

With lithium (2-thienyl)cyanocuprate; In tetrahydrofuran; at -60 ℃; for 0.166667h;

(3S,4R)-3-allyl-4-(tert-butyldimethylsilyloxy)-2-trimethylsilyloxytetrahydrofuran; With trimethylsilyl bromide; In tetrahydrofuran; dichloromethane; at -60 ℃; for 2h;

DOI:10.1021/jo048035v

Reference yield:

(3S,4R)-3-allyl-4-hydroxytetrahydrofuran-2-one (374680-92-9) → [2R,(1E,3R),3R,4R]-3-allyl-4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)-1-butenyl]-tetrahydrofuran (374680-96-3)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; 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-allyl-4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)-1-butenyl]-tetrahydrofuran (374680-96-3)

Guidance literature:

Multi-step reaction with 2 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

With tert.-butyl lithium; triethylamine; In tetrahydrofuran;

DOI:10.1021/jo048035v

upstream raw materials:

(E)-1-iodo-4-(3-chlorophenoxy)-3(R)-(tert-butyldimethylsilyloxy)-1-butene

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

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

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

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

[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

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