(1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol

Base Information

• Chemical Name: (1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol
• CAS No.: 131691-32-2
• Molecular Formula: C₁₆H₃₄O₂Si
• Molecular Weight: 286.53
• Mol file: 131691-32-2.mol

Synonyms:(1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol

Chemical Property of (1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol

There total 4 articles about (1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol 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: 76.0%

(1R,2S,5R)-2-[2'-hydroxy-10-methylethyl]-5-methylcyclohexan-1-ol (200573-67-7) + tert-butyldimethylsilyl chloride (18162-48-6) → (1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol (131691-32-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 0.25h; Inert atmosphere;

DOI:10.1016/j.tet.2013.05.082

Reference yield: 15.0%

(1R,3R,4S,8R)-9-hydroxy-p-menthol (13834-07-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol (131691-32-2) + (R)-2-((1S,2R,4R)-2-((tert-butyldimethylsilyl)oxy)-4-methylcyclohexyl)propan-1-ol

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80810-3

Reference yield:

isopulegol (7786-67-6,18674-65-2,20549-46-6,21290-09-5,29141-10-4,50373-36-9,59905-53-2,59905-54-3,96612-21-4,104870-56-6,121468-66-4,122517-60-6,122517-61-7,144541-38-8,89-79-2) → (1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol (131691-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) B₂H₆, 2.) H₂O₂, NaOH / 1.) THF

2: 4-N,N-dimethylaminopyridine / CH₂Cl₂

With dmap; sodium hydroxide; dihydrogen peroxide; diborane; In dichloromethane;

DOI:10.1039/c39900001487

upstream raw materials:

(1R,3R,4S,8R)-9-hydroxy-p-menthol

tert-butyldimethylsilyl chloride

isopulegol

(1R,2S,5R)-2-[2'-hydroxy-10-methylethyl]-5-methylcyclohexan-1-ol

Downstream raw materials:

(2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-one

5R,6S-dimethyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane

2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethylcyclohexanone

5R,6S-dimethyl-2S-(2'R-propionyl)-1-E/Z-trimethylsilylmethylenecyclohexane