{(4S,6S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl-6-phenethyl-[1,3]dioxan-(5E)-ylidene}-[(S)-2-methoxymethylpyrrolidin-1-yl]-amine

Base Information

• Chemical Name: {(4S,6S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl-6-phenethyl-[1,3]dioxan-(5E)-ylidene}-[(S)-2-methoxymethylpyrrolidin-1-yl]-amine
• CAS No.: 745058-28-0
• Molecular Formula: C₂₈H₄₈N₂O₄Si
• Molecular Weight: 504.786
• Mol file: 745058-28-0.mol

Synonyms:{(4S,6S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl-6-phenethyl-[1,3]dioxan-(5E)-ylidene}-[(S)-2-methoxymethylpyrrolidin-1-yl]-amine

Chemical Property of {(4S,6S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl-6-phenethyl-[1,3]dioxan-(5E)-ylidene}-[(S)-2-methoxymethylpyrrolidin-1-yl]-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(4S,6S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl-6-phenethyl-[1,3]dioxan-(5E)-ylidene}-[(S)-2-methoxymethylpyrrolidin-1-yl]-amine

There total 1 articles about {(4S,6S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl-6-phenethyl-[1,3]dioxan-(5E)-ylidene}-[(S)-2-methoxymethylpyrrolidin-1-yl]-amine 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:

2-phenethyl iodide (17376-04-4) + {(S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl[1,3]dioxan-(5E/Z)-ylidene}-[(S)-2-methoxymethylpyrrolodin-1-yl]-amine → {(4S,6S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl-6-phenethyl-[1,3]dioxan-(5E)-ylidene}-[(S)-2-methoxymethylpyrrolidin-1-yl]-amine (745058-28-0)

Guidance literature:

{(S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl[1,3]dioxan-(5E/Z)-ylidene}-[(S)-2-methoxymethylpyrrolodin-1-yl]-amine; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 2h;

2-phenethyl iodide; In tetrahydrofuran; pentane; at -100 - 20 ℃;

DOI:10.1055/s-2004-822387

Reference yield: 96.0%

{(4S,6S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl-6-phenethyl-[1,3]dioxan-(5E)-ylidene}-[(S)-2-methoxymethylpyrrolidin-1-yl]-amine (745058-28-0) → (4S,6S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl-6-phenethyl-[1,3]dioxan-5-one (745058-30-4)

Guidance literature:

With oxalic acid; In diethyl ether; at 20 ℃; for 4h;

DOI:10.1055/s-2004-822387

Reference yield:

{(4S,6S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl-6-phenethyl-[1,3]dioxan-(5E)-ylidene}-[(S)-2-methoxymethylpyrrolidin-1-yl]-amine (745058-28-0) → 5-{2-[(4R,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-ethylsulfonyl}-1-phenyl-1H-tetrazole (485321-85-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 96 percent / aq. oxalic acid / diethyl ether / 4 h / 20 °C

2.1: NaBH₄ / methanol / 2 h / 0 °C

3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

3.2: tetrahydrofuran / 0.5 h

4.1: 2.033 g / tetrahydrofuran / 20 °C

5.1: Bu₃SnH; AIBN / toluene / 1 h / Heating

6.1: 1.035 g / TBAF / tetrahydrofuran / 5 h / 20 °C

7.1: 84 percent / imidazole; PPh₃; I₂ / diethyl ether; acetonitrile / 1 h / 0 °C

8.1: NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 20 °C

8.2: 99 percent / tetrahydrofuran; dimethylformamide

9.1: 87 percent / MCPBA; NaHCO₃ / CH₂Cl₂ / 48 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; iodine; tri-n-butyl-tin hydride; oxalic acid; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 8.2: Williamson etherification;

DOI:10.1055/s-2004-822387

upstream raw materials:

2-phenethyl iodide

Downstream raw materials:

(4S,6S)-4-[2-(tert-butyldimethylsilanyloxy)ethyl]-2,2-dimethyl-6-phenethyl-[1,3]dioxan-5-one

2-{(4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl}-ethanol

(4S,6S)-4-{(E)-3-[(2R,6R)-6-isopropoxy-3,6-dihydro-2H-pyran-2-yl]-allyl}-2,2-dimethyl-6-phenethyl-[1,3]dioxane

5-{2-[(4R,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-ethylsulfanyl}-1-phenyl-1H-tetrazole