(2S,1'S)-2-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-4H-pyran-4-one

Base Information

Chemical Name:(2S,1'S)-2-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-4H-pyran-4-one
CAS No.:436151-08-5
Molecular Formula:C₁₈H₂₆O₃Si
Molecular Weight:318.488
Hs Code.:

Synonyms:(2S,1'S)-2-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-4H-pyran-4-one

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Chemical Property of (2S,1'S)-2-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-4H-pyran-4-one

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Technology Process of (2S,1'S)-2-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-4H-pyran-4-one

There total 5 articles about (2S,1'S)-2-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-4H-pyran-4-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:

: 54125-02-9
danishefsky's diene

: 133187-22-1
(2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde

: 436150-98-0
(2R,1'S)-2-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-4H-pyran-4-one

: 436151-08-5
(2S,1'S)-2-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-4H-pyran-4-one

Guidance literature:: danishefsky's diene; (2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde; With 4 A molecular sieve; (R,R)-(salen)Cr(III)-BF₄; In various solvent(s); at 4 ℃; for 24h;

With trifluoroacetic acid; In various solvent(s); at 0 - 20 ℃; Further stages. Title compound not separated from byproducts.;
DOI:10.1021/ol0258785

Reference yield:

: (tert-butyl-dimethyl-silanyloxy)-phenyl-acetaldehyde

: 54125-02-9
danishefsky's diene

: (R)-2-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-pyran-4-one

: (S)-2-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-pyran-4-one

: 436150-98-0
(2R,1'S)-2-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-4H-pyran-4-one

: 436151-08-5
(2S,1'S)-2-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-4H-pyran-4-one

Guidance literature:: (tert-butyl-dimethyl-silanyloxy)-phenyl-acetaldehyde; danishefsky's diene; With barium(II) oxide; Schiff base-Cr(III)-Cl; In ethyl acetate; at 4 ℃; for 22.5h;

With trifluoroacetic acid; In ethyl acetate; at 0 - 20 ℃; Further stages. Title compound not separated from byproducts.;
DOI:10.1021/ol0258785

Reference yield:

: 21210-43-5
(S)-Methyl mandelate

: 436151-08-5
(2S,1'S)-2-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,3-dihydro-4H-pyran-4-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / imidazole / dimethylformamide / 18 h / 20 °C

2.1: 82 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

3.1: molecular sieves 4 Angstroem / (S,S) (salen)Cr(III)-BF₄ complex / various solvent(s) / 24 h / 4 °C

3.2: TFA / various solvent(s) / 0 - 20 °C

With 1H-imidazole; 4 A molecular sieve; diisobutylaluminium hydride; (S,S) (salen)Cr(III)-BF₄; In dichloromethane; N,N-dimethyl-formamide; 3.1: hetero-Diels-Alder cycloaddition;
DOI:10.1021/ol0258785