2H-Pyran-2-acetonitrile, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]tetrahydro-6-[(2R)-2-methoxy-4-( phenylmethoxy)butyl]-, (2S,4S,6R)-

Base Information

• Chemical Name: 2H-Pyran-2-acetonitrile, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]tetrahydro-6-[(2R)-2-methoxy-4-( phenylmethoxy)butyl]-, (2S,4S,6R)-
• CAS No.: 850404-94-3
• Molecular Formula: C35H45NO4Si
• Molecular Weight: 571.832
• Mol file: 850404-94-3.mol

Synonyms:

Chemical Property of 2H-Pyran-2-acetonitrile, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]tetrahydro-6-[(2R)-2-methoxy-4-( phenylmethoxy)butyl]-, (2S,4S,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Pyran-2-acetonitrile, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]tetrahydro-6-[(2R)-2-methoxy-4-( phenylmethoxy)butyl]-, (2S,4S,6R)-

There total 8 articles about 2H-Pyran-2-acetonitrile, 4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]tetrahydro-6-[(2R)-2-methoxy-4-( phenylmethoxy)butyl]-, (2S,4S,6R)- 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: 95.0%

{(2S,4S,6S)-6-[(R)-4-benzyloxy-2-methoxybutyl]-4-hydroxytetrahydro-2H-pyran-2-yl}acetonitrile (850404-93-2) + tert-butylchlorodiphenylsilane (58479-61-1) → {(2S,4S,6R)-6-[(R)-4-benzyloxy-2-methoxybutyl]-4-(tert-butyldiphenylsilanyloxy)tetrahydro-2H-pyran-2-yl}acetonitrile (850404-94-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 72 ℃;

DOI:10.1002/anie.200462408

Reference yield:

{(2S,6S)-6-[(R)-4-benzyloxy-2-methoxybutyl]-5,6-dihydro-2H-pyran-2-yl}acetonitrile (850404-92-1) → {(2S,4S,6R)-6-[(R)-4-benzyloxy-2-methoxybutyl]-4-(tert-butyldiphenylsilanyloxy)tetrahydro-2H-pyran-2-yl}acetonitrile (850404-94-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: mercury trifluoroacetate / tetrahydrofuran / 18 h

1.2: 76 percent / NaBH₄; NaOH / tetrahydrofuran

2.1: 95 percent / imidazole / dimethylformamide / 72 h

With 1H-imidazole; mercury(II) trifluoroacetate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo0610412

Reference yield:

(2S,3S)-3-(Dimethyl-phenyl-silanyl)-pent-4-ene-1,2-diol (850405-00-4) → {(2S,4S,6R)-6-[(R)-4-benzyloxy-2-methoxybutyl]-4-(tert-butyldiphenylsilanyloxy)tetrahydro-2H-pyran-2-yl}acetonitrile (850404-94-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 89 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 72 h / 20 °C

2.1: 92 percent / pyridine / tetrahydrofuran / 12 h

3.1: 80 percent / TfOH / CH₂Cl₂ / 12 h / -78 °C

4.1: 87 percent / dimethylformamide / 60 h / 60 °C

5.1: mercury trifluoroacetate / tetrahydrofuran / 18 h

5.2: 76 percent / NaBH₄; NaOH / tetrahydrofuran

6.1: 95 percent / imidazole / dimethylformamide / 72 h

With pyridine; 1H-imidazole; dmap; trifluorormethanesulfonic acid; mercury(II) trifluoroacetate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0610412

upstream raw materials:

{(2S,4S,6S)-6-[(R)-4-benzyloxy-2-methoxybutyl]-4-hydroxytetrahydro-2H-pyran-2-yl}acetonitrile

tert-butylchlorodiphenylsilane

(2S,3S)-3-(Dimethyl-phenyl-silanyl)-pent-4-ene-1,2-diol

{(2S,6S)-6-[(R)-4-benzyloxy-2-methoxybutyl]-5,6-dihydro-2H-pyran-2-yl}acetonitrile

Downstream raw materials:

[4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile

{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-2-methoxy-3-((2R,3S,6S)-3-methyl-6-(oxoethyl)tetrahydro-2H-pyran-2-yl)propyl]tetrahydro-2H-pyran-2-yl}acetonitrile

(2S,5S,6R)-6-{(2S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-cyanomethyltetrahydro-2H-pyran-2-yl]-2-methoxypropyl}-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid isopropyl ester