(R)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2-methyl-cyclohexanone

Base Information

Chemical Name:(R)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2-methyl-cyclohexanone
CAS No.:355387-13-2
Molecular Formula:C₁₇H₃₂O₂Si
Molecular Weight:296.525
Hs Code.:

Synonyms:(R)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2-methyl-cyclohexanone

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Chemical Property of (R)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2-methyl-cyclohexanone

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Technology Process of (R)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2-methyl-cyclohexanone

There total 4 articles about (R)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2-methyl-cyclohexanone 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: 96.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 355387-11-0
(R)-2-((S)-1-Hydroxy-but-3-enyl)-2-methyl-cyclohexanone

: 355387-13-2
(R)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2-methyl-cyclohexanone

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; for 1h;
DOI:10.1002/1521-3765(20010518)7:10<2261::AID-CHEM2261>3.0.CO;2-F

Reference yield:

: 123522-69-0
((R)-6-Methyl-1,4-dioxa-spiro[4.5]dec-6-yl)-methanol

: 355387-13-2
(R)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2-methyl-cyclohexanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: DMSO; oxalyl chloride; DIPEA / CH₂Cl₂ / 1.42 h / -78 - 0 °C

2.1: (-)-DIP-Chloride / diethyl ether / -78 - 25 °C

2.2: diethyl ether; tetrahydrofuran / -78 °C

2.3: aq. NaOH; H₂O₂ / diethyl ether; tetrahydrofuran / 50 °C

3.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

With 2,6-dimethylpyridine; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; dichloromethane; 1.1: Swern oxidation / 2.2: Brown allylation;
DOI:10.1002/1521-3765(20010518)7:10<2261::AID-CHEM2261>3.0.CO;2-F

Reference yield:

: 123522-78-1
(R)-6-Methyl-1,4-dioxa-spiro[4.5]decane-6-carbaldehyde

: 355387-13-2
(R)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-but-3-enyl]-2-methyl-cyclohexanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: (-)-DIP-Chloride / diethyl ether / -78 - 25 °C

1.2: diethyl ether; tetrahydrofuran / -78 °C

1.3: aq. NaOH; H₂O₂ / diethyl ether; tetrahydrofuran / 50 °C

2.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

With 2,6-dimethylpyridine; (-)-diisopinocamphenylborane chloride; In diethyl ether; dichloromethane; 1.2: Brown allylation;
DOI:10.1002/1521-3765(20010518)7:10<2261::AID-CHEM2261>3.0.CO;2-F