(4R,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-chloro-4-methoxy-2-trimethylsilanyloxy-oct-7-enenitrile

Base Information

• Chemical Name: (4R,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-chloro-4-methoxy-2-trimethylsilanyloxy-oct-7-enenitrile
• CAS No.: 913355-79-0
• Molecular Formula: C₂₈H₄₀ClNO₃Si₂
• Molecular Weight: 530.255

Synonyms:(4R,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-chloro-4-methoxy-2-trimethylsilanyloxy-oct-7-enenitrile

Chemical Property of (4R,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-chloro-4-methoxy-2-trimethylsilanyloxy-oct-7-enenitrile

Chemical Property:

Purity/Quality:

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Technology Process of (4R,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-chloro-4-methoxy-2-trimethylsilanyloxy-oct-7-enenitrile

There total 8 articles about (4R,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-chloro-4-methoxy-2-trimethylsilanyloxy-oct-7-enenitrile 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:

tert-butyl-((3R,4R)-4-chloro-3-methoxyhex-5-enyloxy)dimethylsilane (865872-30-6) → (4R,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-chloro-4-methoxy-2-trimethylsilanyloxy-oct-7-enenitrile (913355-79-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: K₃[Fe(CN)6]; hydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether; OsO₄ / 2-methyl-propan-2-ol; H₂O

2.1: pyridine

3.1: potassium carbonate / methanol

4.1: nBuLi / tetrahydrofuran / 0 °C

4.2: tetrahydrofuran / 0 °C

5.1: imidazole

6.1: pyridinium para-toluenesulfonate / methanol

7.1: dimethylsulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - 20 °C

8.1: N-methylmorpholine-N-oxide / CH₂Cl₂

With pyridine; 1H-imidazole; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; 7.1: Swern oxidation;

DOI:10.1002/anie.200601655

Reference yield:

(2R,3R,4R)-6-(tert-butyldimethylsilanyloxy)-3-chloro-4-methoxyhexane-1,2-diol (865872-31-7) → (4R,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-chloro-4-methoxy-2-trimethylsilanyloxy-oct-7-enenitrile (913355-79-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine

2.1: potassium carbonate / methanol

3.1: nBuLi / tetrahydrofuran / 0 °C

3.2: tetrahydrofuran / 0 °C

4.1: imidazole

5.1: pyridinium para-toluenesulfonate / methanol

6.1: dimethylsulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - 20 °C

7.1: N-methylmorpholine-N-oxide / CH₂Cl₂

With pyridine; 1H-imidazole; n-butyllithium; oxalyl dichloride; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 6.1: Swern oxidation;

DOI:10.1002/anie.200601655

Reference yield:

(3R,4R)-1-(tert-butyldimethylsilanyloxy)-4-chlorohex-5-en-3-ol (865872-29-3) → (4R,5S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-5-chloro-4-methoxy-2-trimethylsilanyloxy-oct-7-enenitrile (913355-79-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: proton sponge

2.1: K₃[Fe(CN)6]; hydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether; OsO₄ / 2-methyl-propan-2-ol; H₂O

3.1: pyridine

4.1: potassium carbonate / methanol

5.1: nBuLi / tetrahydrofuran / 0 °C

5.2: tetrahydrofuran / 0 °C

6.1: imidazole

7.1: pyridinium para-toluenesulfonate / methanol

8.1: dimethylsulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - 20 °C

9.1: N-methylmorpholine-N-oxide / CH₂Cl₂

With pyridine; 1H-imidazole; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; Proton Sponge; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; 8.1: Swern oxidation;

DOI:10.1002/anie.200601655

upstream raw materials:

tert-butyl-((3R,4R)-4-chloro-3-methoxyhex-5-enyloxy)dimethylsilane

(3R,4R)-1-(tert-butyldimethylsilanyloxy)-4-chlorohex-5-en-3-ol

(2R,3R,4R)-6-(tert-butyldimethylsilanyloxy)-3-chloro-4-methoxyhexane-1,2-diol

tert-Butyl-((3R,4S)-4-chloro-3-methoxy-4-(R)-oxiranyl-butoxy)-dimethyl-silane

Downstream raw materials:

(5S,8S,9S)-11-Benzyloxy-2-[(2R,3S,4R)-4-(tert-butyl-diphenyl-silanyloxy)-3-chloro-2-methoxy-hex-5-enyl]-8-hydroxy-5-methyl-6-oxo-9-triethylsilanyloxy-2-trimethylsilanyloxy-undecanenitrile

(4R,5S,6R)-2-{(S)-3-[(S)-5-((S)-3-Benzyloxy-1-triethylsilanyloxy-propyl)-4,5-dihydro-isoxazol-3-yl]-butyl}-6-(tert-butyl-diphenyl-silanyloxy)-5-chloro-4-methoxy-2-trimethylsilanyloxy-oct-7-enenitrile

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