2-((1S,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-2-((4-methoxybenzyloxy)methyl)-3-methylcyclopentyl)ethanol

Base Information

• Chemical Name: 2-((1S,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-2-((4-methoxybenzyloxy)methyl)-3-methylcyclopentyl)ethanol
• CAS No.: 1423021-31-1
• Molecular Formula: C₂₃H₄₀O₄Si
• Molecular Weight: 408.654

Synonyms:2-((1S,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-2-((4-methoxybenzyloxy)methyl)-3-methylcyclopentyl)ethanol

Chemical Property of 2-((1S,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-2-((4-methoxybenzyloxy)methyl)-3-methylcyclopentyl)ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((1S,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-2-((4-methoxybenzyloxy)methyl)-3-methylcyclopentyl)ethanol

There total 10 articles about 2-((1S,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-2-((4-methoxybenzyloxy)methyl)-3-methylcyclopentyl)ethanol 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: 55.0%

C23H38O3Si (1423021-30-0) → 2-((1S,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-2-((4-methoxybenzyloxy)methyl)-3-methylcyclopentyl)ethanol (1423021-31-1)

Guidance literature:

C₂₃H₃₈O₃Si; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 10h; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; for 3h; Inert atmosphere;

DOI:10.1002/cjoc.201201039

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → 2-((1S,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-2-((4-methoxybenzyloxy)methyl)-3-methylcyclopentyl)ethanol (1423021-31-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: dihydrogen peroxide; sodium hydroxide / methanol / 0 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 20 °C / Inert atmosphere

3.1: methanol; diethyl ether / 0 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere

5.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / Inert atmosphere

6.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / Inert atmosphere

7.1: sodium periodate / water; acetone / 20 °C / Inert atmosphere

8.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

8.2: Inert atmosphere

9.1: palladium diacetate; triphenylphosphine; tri-n-butyl-tin hydride / tetrahydrofuran / 20 °C / Inert atmosphere

10.1: dimethylsulfide borane complex / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere

10.2: 3 h / Inert atmosphere

With 2,6-dimethylpyridine; potassium osmate(VI) dihydrate; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide borane complex; dihydrogen peroxide; tri-n-butyl-tin hydride; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; triphenylphosphine; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;

DOI:10.1002/cjoc.201201039

Reference yield:

(2R,3S,5S)-2-Chloro-3-hydroxy-5-isopropenyl-2-methyl-cyclohexanone (156714-47-5) → 2-((1S,2S,3R,4S)-4-(tert-butyldimethylsilyloxy)-2-((4-methoxybenzyloxy)methyl)-3-methylcyclopentyl)ethanol (1423021-31-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 20 °C / Inert atmosphere

2.1: methanol; diethyl ether / 0 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere

4.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / Inert atmosphere

5.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / Inert atmosphere

6.1: sodium periodate / water; acetone / 20 °C / Inert atmosphere

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

7.2: Inert atmosphere

8.1: palladium diacetate; triphenylphosphine; tri-n-butyl-tin hydride / tetrahydrofuran / 20 °C / Inert atmosphere

9.1: dimethylsulfide borane complex / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere

9.2: 3 h / Inert atmosphere

With 2,6-dimethylpyridine; potassium osmate(VI) dihydrate; sodium periodate; lithium aluminium tetrahydride; dimethylsulfide borane complex; tri-n-butyl-tin hydride; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-methylmorpholine N-oxide; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;

DOI:10.1002/cjoc.201201039

upstream raw materials:

(S)-p-mentha-6,8-dien-2-one

(2R,3S,5S)-2-Chloro-3-hydroxy-5-isopropenyl-2-methyl-cyclohexanone

C₁₆H₂₉ClO₂Si

C₁₇H₃₂O₃Si

Downstream raw materials:

methyl 2-((1R,2S,3R,4S)-4-hydroxy-2-((4-methoxybenzyloxy)methyl)-3-methylcyclopentyl)acetate

methyl 2-((1R,2S,3R,4S)-2-((4-methoxybenzyloxy)methyl)-3-methyl-4-(methylthiocarbonothioyloxy)cyclopentyl)acetate

methyl 2-((1S,4S,5R)-5-((4-methoxybenzyloxy)methyl)-4-methylcyclopent-2-enyl)acetate

C₁₈H₂₄O₅

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