(R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene

Base Information

• Chemical Name: (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene
• CAS No.: 152187-06-9
• Molecular Formula: C₁₆H₂₉F₃O₄SSi
• Molecular Weight: 402.551
• Mol file: 152187-06-9.mol

Synonyms:(R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene

Chemical Property of (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene

There total 5 articles about (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene 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: 87.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + (4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one (130583-95-8) → (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene (152187-06-9)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 0 ℃; for 14h; Inert atmosphere;

DOI:10.1039/c4ob02144d

Reference yield:

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one (20548-02-1,55058-51-0,60686-81-9,60686-82-0,82977-53-5,90082-06-7,90129-05-8,99881-84-2,60046-50-6) → (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene (152187-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / DMAP; triethylamine / CH₂Cl₂

2: 68 percent / LDA

With dmap; triethylamine; lithium diisopropyl amide; In dichloromethane;

DOI:10.1016/S0040-4020(02)00667-1

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (R)-5-(tert-butyldimethylsilyloxy)-2-[(trifluoromethanesulfonyl)oxy]-1,3,3-trimethylcyclohex-1-ene (152187-06-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 1) iPr₂NLi / 1) THF, hexane, 1 h, -78 deg C, 2) THF, 5 h, 0 deg C

With dmap; triethylamine; lithium diisopropyl amide; In dichloromethane;

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

(4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-2,2,6-trimethylcyclohexan-1-one

(4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexan-1-one

(6R)-levodione

Downstream raw materials:

Methyl (3R,E)-3-(4-tert-Butyldimethylsilyloxy-2,6,6-trimethylcyclohex-1-enyl)prop-2-enoate

(R)-4-ethynyl-3,5,5-trimethylcyclohex-3-en-1-ol

(3R',3'R)-alloxanthin

(3R,3'R)-alloxanthin acetate