(1'R,2'S,4''R)-3-[1'-formyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile

Base Information

• Chemical Name: (1'R,2'S,4''R)-3-[1'-formyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile
• CAS No.: 930795-32-7
• Molecular Formula: C₂₃H₃₉NO₄Si
• Molecular Weight: 421.652
• Mol file: 930795-32-7.mol

Synonyms:(1'R,2'S,4''R)-3-[1'-formyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile

Chemical Property of (1'R,2'S,4''R)-3-[1'-formyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R,2'S,4''R)-3-[1'-formyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile

There total 13 articles about (1'R,2'S,4''R)-3-[1'-formyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile 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: 75.0%

triethylsilyl chloride (994-30-9) + (3aR,7aS,4''R)-3-[6'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-7-methyl-3-oxo-1,4,5,7a-tetrahydroisobenzofuran-3a-yl]propionitrile (645394-01-0) → (1'R,2'S,4''R)-3-[1'-formyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile (930795-32-7)

Guidance literature:

(3aR,7aS,4''R)-3-[6'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-7-methyl-3-oxo-1,4,5,7a-tetrahydroisobenzofuran-3a-yl]propionitrile; With diisobutylaluminium hydride; In diethyl ether; toluene; at -78 ℃; for 0.333333h;

triethylsilyl chloride; With 1H-imidazole; dmap; In dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1021/jo062396o

Reference yield:

C11H18O6 → (1'R,2'S,4''R)-3-[1'-formyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile (930795-32-7)

Guidance literature:

Multi-step reaction with 11 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

With 4-methyl-morpholine; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; 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;

DOI:10.1021/jo062396o

Reference yield:

2,3-O-isopropylidene-L-glyceric acid (102045-96-5,62075-55-2) → (1'R,2'S,4''R)-3-[1'-formyl-4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile (930795-32-7)

Guidance literature:

Multi-step reaction with 12 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

With 4-methyl-morpholine; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; 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; 4.2: Wittig olefination / 9.1: Swern oxidation / 10.2: Horner-Wadsworth-Emmons condensation;

DOI:10.1021/jo062396o

upstream raw materials:

triethylsilyl chloride

(3aR,7aS,4''R)-3-[6'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-7-methyl-3-oxo-1,4,5,7a-tetrahydroisobenzofuran-3a-yl]propionitrile

2,3-O-isopropylidene-L-glyceric acid

methyl (4S)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

Downstream raw materials:

(1'R,2'S,4''R)-3-[4'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-methyl-1'-(1'''-hydroxyallyl)-2'-triethylsilanyloxymethylcyclohex-3'-enyl]propionitrile

1-((1R,2S)-1-(2-cyanoethyl)-2-(triethylsilanyloxymethyl)-3-methyl-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)cyclohex-3-enyl)allyl 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