(4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate

Base Information

• Chemical Name: (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate
• CAS No.: 930795-40-7
• Molecular Formula: C₄₇H₈₅NO₇Si₂
• Molecular Weight: 832.365
• Mol file: 930795-40-7.mol

Synonyms:(4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate

Chemical Property of (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate

There total 46 articles about (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate 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:

(2R,4R,5R)-[3-(5-((E)-1-iodoprop-1-en-2-yl)-4-methyltetrahydrofuran-2-yl)propoxy]triisopropylsilane (930795-11-2) + acetic acid 3-(9-bora-bicyclo[3.3.1]non-9-yl)-1-[1-(2-cyano-ethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-cyclohex-3-enyl]-propyl ester → (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate (930795-40-7)

Guidance literature:

acetic acid 3-(9-bora-bicyclo[3.3.1]non-9-yl)-1-[1-(2-cyano-ethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-2-triethylsilanyloxymethyl-cyclohex-3-enyl]-propyl ester; With water; In tetrahydrofuran; at 20 ℃; for 1h;

(2R,4R,5R)-[3-(5-((E)-1-iodoprop-1-en-2-yl)-4-methyltetrahydrofuran-2-yl)propoxy]triisopropylsilane; With triphenyl-arsane; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; N,N-dimethyl-formamide; at 20 ℃; for 10h;

DOI:10.1021/jo062396o

Reference yield:

C11H18O6 → (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate (930795-40-7)

Guidance literature:

Multi-step reaction with 15 steps

1.1: N-methylmorpholine

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 71 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

3.2: 84 percent / tetrahydrofuran; hexane / 5 h / 0 °C

4.1: glacial acetic acid / ethanol / 48 h / 20 °C

5.1: DDQ / CH₂Cl₂; H₂O / 8 h / 20 °C / pH 7

6.1: NaBH₄ / tetrahydrofuran; H₂O / 6 h / -10 °C

7.1: 110 mg / Et₃N; ClCOOMe / tetrahydrofuran / 60 h / 20 °C

8.1: 89 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 0.67 h / 0 - 20 °C

9.2: 85 percent / tetrahydrofuran; hexane / 2 h / 20 °C

10.1: 80 percent / H₂ / Pd/C / ethyl acetate / 12 h / 0 °C

11.1: DIBAL-H / diethyl ether; toluene / 0.33 h / -78 °C

11.2: 75 percent / DMAP; imidazole / CH₂Cl₂ / 0.33 h / 20 °C

12.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C

13.1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

14.1: tetrahydrofuran / 3 h / 20 °C

15.1: H₂O / tetrahydrofuran / 1 h / 20 °C

15.2: 28.1 mg / Cs₂CO₃; AsPh₃ / PdCl₂(dppf) / dimethylformamide; H₂O; tetrahydrofuran / 10 h / 20 °C

With 4-methyl-morpholine; dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; water; hydrogen; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; methyl chloroformate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; ethyl acetate; toluene; 3.2: Wittig olefination / 8.1: Swern oxidation / 9.2: Horner-Wadsworth-Emmons condensation / 15.2: Suzuki-Miyaura coupling;

DOI:10.1021/jo062396o

Reference yield:

(2S,4R,5R)-5-(tert-butyldimethylsilanyloxymethyl)-4-methyltetrahydrofuran-2-carbaldehyde (930795-06-5) → (4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate (930795-40-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 - 20 °C

1.2: 82 percent / tetrahydrofuran; hexane / 1 h / 20 °C

2.1: H₂ / Pd/C / ethanol / 12 h / 20 °C

3.1: 12 mg / TBAF / tetrahydrofuran / 3 h / 20 °C

4.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.17 h / -78 - 0 °C

5.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h / -78 °C

5.2: 4.1 mg / tetrahydrofuran / -78 - 20 °C

6.1: LiAlH₄ / diethyl ether / 1 h / cooling

7.1: 37.2 mg / imidazole; DMAP / CH₂Cl₂ / 20 °C

8.1: n-Bu₃SnCu(CN)Li / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: DMPU / tetrahydrofuran; hexane / -78 - 20 °C

8.3: 89 percent / iodine / diethyl ether / 0.5 h / 20 °C

9.1: H₂O / tetrahydrofuran / 1 h / 20 °C

9.2: 28.1 mg / Cs₂CO₃; AsPh₃ / PdCl₂(dppf) / dimethylformamide; H₂O; tetrahydrofuran / 10 h / 20 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; n-Bu₃SnCu(CN)Li; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; 4.1: Swern oxidation / 9.2: Suzuki-Miyaura coupling;

DOI:10.1021/jo062396o

upstream raw materials:

(2R,4R,5R)-[3-(5-((E)-1-iodoprop-1-en-2-yl)-4-methyltetrahydrofuran-2-yl)propoxy]triisopropylsilane

(2S,4R,5R)-5-(tert-butyldimethylsilanyloxymethyl)-4-methyltetrahydrofuran-2-carbaldehyde

(2'R,4'R,5'R)-3-[5'-ethynyl-4'-methyltetrahydrofuran-2'-yl]propionic acid ethyl ester

(2'R,4'R,5'R)-3-[5'-hydroxymethyl-4'-methyltetrahydrofuran-2'-yl]propionic acid ethyl ester

Downstream raw materials:

(4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-ethynyl-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate

acetic acid 1-[1-(2-cyano-ethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2-formyl-3-methyl-cyclohex-3-enyl]-5-[3-methyl-5-(3-triisopropylsilanyloxy-propyl)-tetrahydro-furan-2-yl]-hex-4-enyl ester

(4E)-1-((1R,2S)-1-(2-cyanoethyl)-2-(hydroxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)-5-((2R,3R,5R)-5-(3-triisopropylsilanyloxypropyl)-3-methyltetrahydrofuran-2-yl)hex-4-enyl acetate