(3R,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanenitrile

Base Information

• Chemical Name: (3R,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanenitrile
• CAS No.: 1403354-24-4
• Molecular Formula: C₁₉H₂₉NO₂
• Molecular Weight: 303.445
• Mol file: 1403354-24-4.mol

Synonyms:(3R,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanenitrile

Chemical Property of (3R,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanenitrile

There total 10 articles about (3R,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanenitrile 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:

sodium cyanide (773837-37-9) + C25H36O5S → (3R,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanenitrile (1403354-24-4)

Guidance literature:

With sodium iodide; In dimethyl sulfoxide; at 90 ℃; for 1h;

DOI:10.1021/jo301425c

Reference yield:

(S)-(-)-2-methyl-4-penten-1-ol (5673-98-3,63501-27-9,88080-30-2,63501-26-8) → (3R,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanenitrile (1403354-24-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: triethylamine; dmap / dichloromethane / 12 h / 0 - 20 °C

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 10 h / 0 - 20 °C

3.1: (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; acetic acid; water / toluene / 24 h / 20 °C / Cooling with ice

4.1: copper(l) iodide / tetrahydrofuran / 0.08 h / -20 °C / Inert atmosphere

4.2: 1 h / -40 - -20 °C / Inert atmosphere

5.1: potassium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C

6.1: (R,R)-Jacobsen catalyst; acetic acid; water / toluene / 24 h / 20 °C / Cooling with ice

7.1: copper(l) iodide / tetrahydrofuran / 1 h / -40 - 20 °C

8.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 2 h / 0 - 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

10.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C

11.1: sodium iodide / dimethyl sulfoxide / 1 h / 90 °C

With dmap; copper(l) iodide; (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; (R,R)-Jacobsen catalyst; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; water; potassium hydride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; dichloromethane; cyclohexane; dimethyl sulfoxide; toluene;

DOI:10.1021/jo301425c

Reference yield:

tert-butyl((S)-2-methyl-3-(oxiran-2-yl)propoxy)diphenylsilane → (3R,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanenitrile (1403354-24-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; acetic acid; water / toluene / 24 h / 20 °C / Cooling with ice

2.1: 2,4,6-trimethyl-pyridine; acetyl chloride / dichloromethane / 10.17 h / -78 °C

2.2: 2.17 h / 0 - 20 °C

2.3: 1 h / Inert atmosphere

3.1: copper(l) iodide / tetrahydrofuran / 0.08 h / -20 °C / Inert atmosphere

3.2: 1 h / -40 - -20 °C / Inert atmosphere

4.1: potassium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C

5.1: (R,R)-Jacobsen catalyst; acetic acid; water / toluene / 24 h / 20 °C / Cooling with ice

6.1: copper(l) iodide / tetrahydrofuran / 1 h / -40 - 20 °C

7.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 2 h / 0 - 20 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

9.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C

10.1: sodium iodide / dimethyl sulfoxide / 1 h / 90 °C

With 2,4,6-trimethyl-pyridine; dmap; copper(l) iodide; (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; (R,R)-Jacobsen catalyst; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; water; potassium hydride; acetic acid; triethylamine; acetyl chloride; sodium iodide; In tetrahydrofuran; dichloromethane; cyclohexane; dimethyl sulfoxide; toluene;

DOI:10.1021/jo301425c

upstream raw materials:

(S)-(-)-2-methyl-4-penten-1-ol

tert-butyl((S)-2-methyl-3-((S)-oxiran-2-yl)propoxy)diphenylsilane

sodium cyanide

(2R,4S)-5-(tert-butyldiphenylsilyloxy)-4-methylpentane-1,2-diol

Downstream raw materials:

(3S,9R,11S,13S,E)-1,13-bis(benzyloxy)-3-hydroxy-11-methoxy-9-methylhexadec-6-en-5-one

(2R,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one

(2S,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one

(3S,9R,11S,13S,E)-1,13-bis(benzyloxy)-3-(tert-butyldimethylsilyloxy)-11-methoxy-9-methylhexadec-6-en-5-one