methyl (1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-6-oxo-cyclohexanecarboxylate

Base Information

• Chemical Name: methyl (1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-6-oxo-cyclohexanecarboxylate
• CAS No.: 309243-65-0
• Molecular Formula: C₁₆H₃₀O₄Si
• Molecular Weight: 314.497
• Mol file: 309243-65-0.mol

Synonyms:methyl (1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-6-oxo-cyclohexanecarboxylate

Chemical Property of methyl (1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-6-oxo-cyclohexanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-6-oxo-cyclohexanecarboxylate

There total 5 articles about methyl (1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-6-oxo-cyclohexanecarboxylate 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: 91.0%

methyl cyanoformate (17640-15-2) + methyllithium (917-54-4) + (R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one (309243-64-9) → methyl (1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-6-oxo-cyclohexanecarboxylate (309243-65-0)

Guidance literature:

methyllithium; (R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one; With copper(l) iodide; In diethyl ether; at -5 - 0 ℃; for 1h;

methyl cyanoformate; With N,N,N,N,N,N-hexamethylphosphoric triamide; In diethyl ether; at -70 - 20 ℃;

DOI:10.1016/S0040-4020(00)00645-1

Reference yield:

4-hydroxy-3-methyl-cyclohex-2-en-1-one (57356-79-3) → methyl (1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-6-oxo-cyclohexanecarboxylate (309243-65-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Mucor miehei lipase / diisopropyl ether / 48 h / 20 °C

2.1: 92 percent / imidazole / dimethylformamide / 3 h / 20 °C

3.1: copper(I) iodide / diethyl ether / 1 h / -5 - 0 °C

3.2: 91 percent / HMPA / diethyl ether / -70 - 20 °C

With 1H-imidazole; copper(l) iodide; Mucor miehei lipase; In diethyl ether; di-isopropyl ether; N,N-dimethyl-formamide; 1.1: Acetylation / 2.1: silylation / 3.1: Methylation / 3.2: Addition;

DOI:10.1016/S0040-4020(00)00645-1

Reference yield:

(R)-4-hydroxy-3-methyl-cyclohex-2-en-1-one (184653-97-2) → methyl (1S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2,2-dimethyl-6-oxo-cyclohexanecarboxylate (309243-65-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / imidazole / dimethylformamide / 3 h / 20 °C

2.1: copper(I) iodide / diethyl ether / 1 h / -5 - 0 °C

2.2: 91 percent / HMPA / diethyl ether / -70 - 20 °C

With 1H-imidazole; copper(l) iodide; In diethyl ether; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Methylation / 2.2: Addition;

DOI:10.1016/S0040-4020(00)00645-1

upstream raw materials:

methyl cyanoformate

methyllithium

(R)-4-[(tert-butyldimethylsilyl)oxy]-3-methyl-cyclohex-2-en-1-one

4-hydroxy-3-methyl-cyclohex-2-en-1-one

Downstream raw materials:

(1S,5R)-cis-3-hydroxy-2,2-dimethyl-6-methylenecyclohexanemethanol