(1R,2R)-2-<2-(t-Butyldiphenylsiloxy)ethyl>-2-methyl-1-cyclobutyl methyl ketone

Base Information

• Chemical Name: (1R,2R)-2-<2-(t-Butyldiphenylsiloxy)ethyl>-2-methyl-1-cyclobutyl methyl ketone
• CAS No.: 135253-39-3
• Molecular Formula: C₂₅H₃₄O₂Si
• Molecular Weight: 394.629
• Mol file: 135253-39-3.mol

Synonyms:(1R,2R)-2-<2-(t-Butyldiphenylsiloxy)ethyl>-2-methyl-1-cyclobutyl methyl ketone

Chemical Property of (1R,2R)-2-<2-(t-Butyldiphenylsiloxy)ethyl>-2-methyl-1-cyclobutyl methyl ketone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-2-<2-(t-Butyldiphenylsiloxy)ethyl>-2-methyl-1-cyclobutyl methyl ketone

There total 14 articles about (1R,2R)-2-<2-(t-Butyldiphenylsiloxy)ethyl>-2-methyl-1-cyclobutyl methyl ketone 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%

1-{(1R,2R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-cyclobutyl}-ethanol (135253-38-2) → (1R,2R)-2-<2-(t-Butyldiphenylsiloxy)ethyl>-2-methyl-1-cyclobutyl methyl ketone (135253-39-3)

Guidance literature:

With Celite; pyridinium chlorochromate; In dichloromethane; for 4h;

DOI:10.1246/bcsj.64.1471

Reference yield:

(1R,6R)-2,6-Dimethyl-3-oxybicyclo<4.2.0>octan-4-one (28117-19-3) → (1R,2R)-2-<2-(t-Butyldiphenylsiloxy)ethyl>-2-methyl-1-cyclobutyl methyl ketone (135253-39-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / LiAlH₄ / tetrahydrofuran / 0.08 h

2: 90 percent / NEt₃, 4-dimethylaminopyridine / CH₂Cl₂; dimethylformamide

3: 91 percent / pyridinium chlorochromate, celite / CH₂Cl₂ / 4 h

With dmap; lithium aluminium tetrahydride; Celite; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.64.1471

Reference yield:

(S)-<2,2-Bis(methylthio)-1-cyclobutyl>methanol (135356-01-3) → (1R,2R)-2-<2-(t-Butyldiphenylsiloxy)ethyl>-2-methyl-1-cyclobutyl methyl ketone (135253-39-3)

Guidance literature:

Multi-step reaction with 12 steps

1: NEt₃, 4-dimethylaminopyridine / CH₂Cl₂

2: 95 percent / AgNO₃, N-chlorosuccinimide / acetonitrile / 0.08 h / 0 °C

3: LiN(c-Hex)2 / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 1 h

4: PhSLi / tetrahydrofuran

5: 96 percent / conc. HCl / methanol / 3.5 h / Ambient temperature

6: 95 percent / NEt₃, 4-dimethylaminopyridine / CH₂Cl₂ / Ambient temperature

7: TMSOTf / diethyl ether / -78 °C

8: pyridinium chlorochromate, celite / CH₂Cl₂ / 3 h

9: diethyl ether / 0.25 h

10: 93 percent / LiAlH₄ / tetrahydrofuran / 0.08 h

11: 90 percent / NEt₃, 4-dimethylaminopyridine / CH₂Cl₂; dimethylformamide

12: 91 percent / pyridinium chlorochromate, celite / CH₂Cl₂ / 4 h

With hydrogenchloride; dmap; N-chloro-succinimide; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; Celite; lithium thiophenoxide; lithium dicyclohexylamide; silver nitrate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1246/bcsj.64.1471

upstream raw materials:

1-{(1R,2R)-2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-cyclobutyl}-ethanol

(1R,6R)-2,6-Dimethyl-3-oxybicyclo<4.2.0>octan-4-one

(S)-<2,2-Bis(methylthio)-1-cyclobutyl>methanol

Methyl <(R),(E)-2-hydroxymethyl-1-cyclobutylidene>acetate

Downstream raw materials:

tert-Butyl-[2-((1R,2S)-2-isopropenyl-1-methyl-cyclobutyl)-ethoxy]-diphenyl-silane

(1R, 2S)-grandisol