(5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-5,6-dihydro-pyran-2-one

Base Information

Chemical Name:(5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-5,6-dihydro-pyran-2-one
CAS No.:753016-53-4
Molecular Formula:C₂₃H₂₈O₃Si
Molecular Weight:380.559
Hs Code.:

Synonyms:(5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-5,6-dihydro-pyran-2-one

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Chemical Property of (5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-5,6-dihydro-pyran-2-one

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Technology Process of (5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-5,6-dihydro-pyran-2-one

There total 7 articles about (5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-5,6-dihydro-pyran-2-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: 57.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 753016-52-3
(Z)-(S)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-pent-2-enoic acid methyl ester

: 753016-53-4
(5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-5,6-dihydro-pyran-2-one

Guidance literature:: (Z)-(S)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-pent-2-enoic acid methyl ester; With Dowex 50W X₈; In methanol; at 20 ℃; for 7h;

With Amberlyst 15; In dichloromethane; at 20 ℃; for 12h;

tert-butylchlorodiphenylsilane; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
DOI:10.1021/ol049219z

Reference yield:

: 71565-21-4
(2S,4'R)-(+)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1-propanol

: 753016-53-4
(5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

2.1: PPh₃; Zn powder / CH₂Cl₂ / 24 h / 20 °C

2.2: 440.7 mg / CH₂Cl₂ / 2 h / 20 °C

3.1: BuLi / tetrahydrofuran; hexane / -78 - 20 °C

3.2: 93 percent / tetrahydrofuran / -78 - 20 °C

4.1: 96 percent / H₂ / Lindlar catalyst / methanol / 20 h / 20 °C

5.1: Dowex 50W X₈ / methanol / 7 h / 20 °C

5.2: Amberlyst 15 / CH₂Cl₂ / 12 h / 20 °C

5.3: 57 percent / imidazole / dimethylformamide / 4 h / 20 °C

With n-butyllithium; Dowex 50W X₈; hydrogen; Dess-Martin periodane; triphenylphosphine; zinc; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ol049219z

Reference yield:

: 77398-87-9
(2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanal

: 753016-53-4
(5S,6R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methyl-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: PPh₃; Zn powder / CH₂Cl₂ / 24 h / 20 °C

1.2: 440.7 mg / CH₂Cl₂ / 2 h / 20 °C

2.1: BuLi / tetrahydrofuran; hexane / -78 - 20 °C

2.2: 93 percent / tetrahydrofuran / -78 - 20 °C

3.1: 96 percent / H₂ / Lindlar catalyst / methanol / 20 h / 20 °C

4.1: Dowex 50W X₈ / methanol / 7 h / 20 °C

4.2: Amberlyst 15 / CH₂Cl₂ / 12 h / 20 °C

4.3: 57 percent / imidazole / dimethylformamide / 4 h / 20 °C

With n-butyllithium; Dowex 50W X₈; hydrogen; triphenylphosphine; zinc; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ol049219z