anti-(1RS,2RS)-2,4,4-Trimethyl-1-<(trimethylsilyl)oxy>-1-phenylpentan-3-one

Base Information

• Chemical Name: anti-(1RS,2RS)-2,4,4-Trimethyl-1-<(trimethylsilyl)oxy>-1-phenylpentan-3-one
• CAS No.: 72658-27-6
• Molecular Formula: C₁₇H₂₈O₂Si
• Molecular Weight: 292.494
• Mol file: 72658-27-6.mol

Synonyms:

Chemical Property of anti-(1RS,2RS)-2,4,4-Trimethyl-1-<(trimethylsilyl)oxy>-1-phenylpentan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of anti-(1RS,2RS)-2,4,4-Trimethyl-1-<(trimethylsilyl)oxy>-1-phenylpentan-3-one

There total 4 articles about anti-(1RS,2RS)-2,4,4-Trimethyl-1-<(trimethylsilyl)oxy>-1-phenylpentan-3-one 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%

(Z)-(4,4-dimethylpent-2-en-3-yloxy)trimethylsilane (61878-68-0) + benzaldehyde (100-52-7) → (1S,2R)-2,4,4-Trimethyl-1-phenyl-1-trimethylsilanyloxy-pentan-3-one (72658-27-6) + (1S,2S)-2,4,4-Trimethyl-1-phenyl-1-trimethylsilanyloxy-pentan-3-one (61878-69-1)

Guidance literature:

With trimethyl(benzyl)ammonium fluoride; In tetrahydrofuran; for 8h; Ambient temperature;

DOI:10.1021/jo01294a030

Reference yield:

(Z)-(4,4-dimethylpent-2-en-3-yloxy)trimethylsilane (61878-68-0) + benzaldehyde (100-52-7) → anti-(1RS,2RS)-2,4,4-Trimethyl-1-<(trimethylsilyl)oxy>-1-phenylpentan-3-one (117775-79-8,117775-80-1,61878-69-1,72658-27-6)

Guidance literature:

With zinc trifluoromethanesulfonate; In acetonitrile; for 3.5h; Yield given; Ambient temperature;

Reference yield:

chloro-trimethyl-silane (75-77-4) + syn-carbonyl{bis(trimethylphosphine)}rhodium aldolate (117800-26-7) → trans-carbonylchlorobis(trimethylphosphine)rhodium (36713-95-8,22710-50-5,133577-23-8) + (1S,2R)-2,4,4-Trimethyl-1-phenyl-1-trimethylsilanyloxy-pentan-3-one (72658-27-6)

Guidance literature:

In benzene; Addition of trimethylsilyl chloride to a benzene soln. of purified (Z)-aldolate at 25°C.; 89:11 Z/E mixt. of silylated aldol;

DOI:10.1021/ja00185a025

upstream raw materials:

(Z)-(4,4-dimethylpent-2-en-3-yloxy)trimethylsilane

benzaldehyde

chloro-trimethyl-silane

syn-carbonyl{bis(trimethylphosphine)}rhodium aldolate

Refernces

• 1、 Slough, Greg A.,Bergman, Robert G.,Heathcock, Clayton H.. "Synthesis of η1 Oxygen-Bound Rhodium Enolates. Applications to Catalytic Aldol Chemistry". . p. 938 - 949. Retrieved 2007/10/02.