(1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-2-methoxy-4-(1-propynyl)cyclohexane

Base Information

• Chemical Name: (1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-2-methoxy-4-(1-propynyl)cyclohexane
• CAS No.: 155386-29-1
• Molecular Formula: C₁₆H₃₀O₂Si
• Molecular Weight: 282.498
• Mol file: 155386-29-1.mol

Synonyms:(1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-2-methoxy-4-(1-propynyl)cyclohexane

Chemical Property of (1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-2-methoxy-4-(1-propynyl)cyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-2-methoxy-4-(1-propynyl)cyclohexane

There total 12 articles about (1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-2-methoxy-4-(1-propynyl)cyclohexane 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: 93.0%

(1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-ethynyl-2-methoxycyclohexane (155386-28-0) + methyl iodide (74-88-4) → (1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-2-methoxy-4-(1-propynyl)cyclohexane (155386-29-1)

Guidance literature:

(1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-ethynyl-2-methoxycyclohexane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -35 ℃; for 2.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; hexane; at -78 ℃; for 12h; Inert atmosphere;

Reference yield:

(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one (216662-57-6) → (1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-2-methoxy-4-(1-propynyl)cyclohexane (155386-29-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: potassium hydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

1.2: 0.5 h / Inert atmosphere

1.3: 0.5 h / 0 °C / Inert atmosphere

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.67 h / 105 °C / Inert atmosphere

3.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / benzene / 1.5 h / Reflux; Inert atmosphere

4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / 110 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / 2.5 h / 53 °C / Inert atmosphere

6.1: 2,6-di-tert-butyl-pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

7.1: methanol; potassium carbonate / 2.5 h / 50 °C / Inert atmosphere

8.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 20 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / hexane / 1.5 h / -78 °C / Inert atmosphere

10.1: triphenylphosphine / dichloromethane / 0.67 h / 0 °C / Inert atmosphere

11.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

12.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - -35 °C / Inert atmosphere

12.2: 12 h / -78 °C / Inert atmosphere

With 1H-imidazole; methanol; N-Bromosuccinimide; n-butyllithium; 2,6-di-tert-butyl-pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

Reference yield:

(1R,3R,4R) methyl 4-hydroxy-3-methoxy-1-cyclohexanecarboxylate (128684-89-9) → (1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-2-methoxy-4-(1-propynyl)cyclohexane (155386-29-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane / 1.5 h / -78 °C / Inert atmosphere

3.1: triphenylphosphine / dichloromethane / 0.67 h / 0 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -78 - -35 °C / Inert atmosphere

5.2: 12 h / -78 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

(1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-(2,2-dibromovinyl)-2-methoxycyclohexane

(1R,2R,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-ethynyl-2-methoxycyclohexane

methyl iodide

(1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one