(3R,5R,6S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

Base Information

• Chemical Name: (3R,5R,6S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile
• CAS No.: 224580-06-7
• Molecular Formula: C₂₉H₅₃NO₄Si₂
• Molecular Weight: 535.915
• Mol file: 224580-06-7.mol

Synonyms:(3R,5R,6S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

Chemical Property of (3R,5R,6S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R,6S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

There total 11 articles about (3R,5R,6S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile 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%

t-butyldimethylsiyl triflate (69739-34-0) + (3R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile (224579-95-7) → (3R,5R,6S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile (224580-06-7)

Guidance literature:

With 2,6-dimethylpyridine;

DOI:10.1016/S0040-4039(99)00207-5

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (3R,5R,6S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile (224580-06-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 93 percent / CSA / CH₂Cl₂

2: 86 percent / DIBAL / CH₂Cl₂

3: 97 percent / 2,6-lutidine

4: 1.) O₃, pyr., 2.) Me₂S / 12 h

5: NaBH₄ / ethanol

6: Bu₃P

7: H₂O₂ / tetrahydrofuran

8: K₂OsO₄*H₂O, DHQ₂-PYR / 24 h

9: 86 percent / NaH, tosylimidazole / tetrahydrofuran

10: 91 percent / LiClO₄ / acetonitrile / 12 h / 70 °C

11: 95 percent / 2,6-lutidine

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; potassium osmate(VI); (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); dimethylsulfide; tributylphosphine; camphor-10-sulfonic acid; dihydrogen peroxide; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; ozone; N-tosylimidazole; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(99)00207-5

Reference yield:

(4R,5S)-2-(4-Methoxy-phenyl)-4,5-dimethyl-4-(4-methyl-pent-3-enyl)-[1,3]dioxane (224580-02-3) → (3R,5R,6S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile (224580-06-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 86 percent / DIBAL / CH₂Cl₂

2: 97 percent / 2,6-lutidine

3: 1.) O₃, pyr., 2.) Me₂S / 12 h

4: NaBH₄ / ethanol

5: Bu₃P

6: H₂O₂ / tetrahydrofuran

7: K₂OsO₄*H₂O, DHQ₂-PYR / 24 h

8: 86 percent / NaH, tosylimidazole / tetrahydrofuran

9: 91 percent / LiClO₄ / acetonitrile / 12 h / 70 °C

10: 95 percent / 2,6-lutidine

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; potassium osmate(VI); (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); dimethylsulfide; tributylphosphine; dihydrogen peroxide; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; ozone; N-tosylimidazole; In tetrahydrofuran; ethanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(99)00207-5

upstream raw materials:

t-butyldimethylsiyl triflate

(3R,5R,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanenitrile

p-Anisaldehyde dimethyl acetal

(4R,5S)-2-(4-Methoxy-phenyl)-4,5-dimethyl-4-(4-methyl-pent-3-enyl)-[1,3]dioxane

Downstream raw materials:

(3S,5R,6S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-5,6-dimethyl-heptanal

[(4S,6R,7S)-4,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-6,7-dimethyl-2-oxo-octyl]-phosphonic acid dimethyl ester

(E)-(2S,4R,9S,11R,12S)-9,13-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,11,12-trimethyl-2-triisopropylsilanyloxy-tridec-5-en-7-one

(2S,3R,5S,8R,9S,10R,12S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one