(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

Base Information

Chemical Name:(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
CAS No.:847563-66-0
Molecular Formula:C₃₃H₅₅ClO₆Si₂
Molecular Weight:639.42
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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: 94.0%

: 17857-14-6
(3-carboxypropyl)(triphenyl)phosphonium bromide

: 374680-98-5
[2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propionaldehyde

: 847563-66-0
(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

Guidance literature:: (3-carboxypropyl)(triphenyl)phosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 3 ℃; for 0.666667h;

[2R,(1E,3R),3R,4R]-3-{4-tert-butyldimethylsilyloxy-2-[3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1-enyl]tetrahydrofuran-3-yl}propionaldehyde; In tetrahydrofuran; at -2 ℃; for 1h;
DOI:10.1021/jo048035v

Reference yield:

: 374680-92-9
(3S,4R)-3-allyl-4-hydroxytetrahydrofuran-2-one

: 847563-66-0
(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

Guidance literature:: Multi-step reaction with 7 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

6.1: 92 percent / dimethyl sulfoxide; triethylamine; oxalyl chloride / CH₂Cl₂ / -60 - 20 °C

7.1: potassium tert-butoxide / tetrahydrofuran / 0.67 h / 3 °C

7.2: 94 percent / tetrahydrofuran / 1 h / -2 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; potassium tert-butylate; tert.-butyl lithium; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 6.1: Swern oxidation;
DOI:10.1021/jo048035v

Reference yield:

: 374680-94-1
(3S,4R)-3-allyl-4-(tert-butyldimethylsilyloxy)tetrahydrofuran-2-ol

: 847563-66-0
(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

Guidance literature:: Multi-step reaction with 5 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

4.1: 92 percent / dimethyl sulfoxide; triethylamine; oxalyl chloride / CH₂Cl₂ / -60 - 20 °C

5.1: potassium tert-butoxide / tetrahydrofuran / 0.67 h / 3 °C

5.2: 94 percent / tetrahydrofuran / 1 h / -2 °C

With 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; potassium tert-butylate; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 4.1: Swern oxidation;
DOI:10.1021/jo048035v