1,1-Dimethylethyl (3R,5S)-3,5-di-[(1',1'-dimethylethyl)-diphenylsilyloxy]-6-oxohexanoate

Base Information

Chemical Name:1,1-Dimethylethyl (3R,5S)-3,5-di-[(1',1'-dimethylethyl)-diphenylsilyloxy]-6-oxohexanoate
CAS No.:123477-30-5
Molecular Formula:C₄₂H₅₄O₅Si₂
Molecular Weight:695.059
Hs Code.:

Synonyms:1,1-Dimethylethyl (3R,5S)-3,5-di-[(1',1'-dimethylethyl)-diphenylsilyloxy]-6-oxohexanoate

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Chemical Property of 1,1-Dimethylethyl (3R,5S)-3,5-di-[(1',1'-dimethylethyl)-diphenylsilyloxy]-6-oxohexanoate

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Technology Process of 1,1-Dimethylethyl (3R,5S)-3,5-di-[(1',1'-dimethylethyl)-diphenylsilyloxy]-6-oxohexanoate

There total 6 articles about 1,1-Dimethylethyl (3R,5S)-3,5-di-[(1',1'-dimethylethyl)-diphenylsilyloxy]-6-oxohexanoate 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: 90.0%

: 123492-49-9
1,1-Dimethylethyl (3R,5S)-3,5-di[(1-,1-dimethylethyl)diphenylsilyloxy]-6-hydroxyhexanoate

: 123477-30-5
1,1-Dimethylethyl (3R,5S)-3,5-di-[(1',1'-dimethylethyl)-diphenylsilyloxy]-6-oxohexanoate

Guidance literature:: With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; at 25 ℃; for 1h;
DOI:10.1016/S0957-4166(00)86320-X

Reference yield:

: 150942-98-6
t-butyl lithioacetate

: 123477-30-5
1,1-Dimethylethyl (3R,5S)-3,5-di-[(1',1'-dimethylethyl)-diphenylsilyloxy]-6-oxohexanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / tetrahydrofuran / -78 - 0 °C

2: Me₄NHB(OAc)3 / tetrahydrofuran; acetic acid / 18 h / 0 °C

3: imidazole / dimethylformamide / 18 h / 70 °C

4: 70 percent / aq. trifluoroacetic acid / CH₂Cl₂ / 2.5 h / 0 - 25 °C

5: 90 percent / pyridinium chlorochromate, 4A molecular sieves / CH₂Cl₂ / 1 h / 25 °C

With 1H-imidazole; 4 A molecular sieve; pyridinium chlorochromate; trifluoroacetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(00)86320-X

Reference yield:

: 113240-61-2
1,1-Dimethylethyl (S)-5-hydroxy-3-oxo-6-(triphenylmethoxy)hexanoate

: 123477-30-5
1,1-Dimethylethyl (3R,5S)-3,5-di-[(1',1'-dimethylethyl)-diphenylsilyloxy]-6-oxohexanoate

Guidance literature:: Multi-step reaction with 4 steps

1: Me₄NHB(OAc)3 / tetrahydrofuran; acetic acid / 18 h / 0 °C

2: imidazole / dimethylformamide / 18 h / 70 °C

3: 70 percent / aq. trifluoroacetic acid / CH₂Cl₂ / 2.5 h / 0 - 25 °C

4: 90 percent / pyridinium chlorochromate, 4A molecular sieves / CH₂Cl₂ / 1 h / 25 °C

With 1H-imidazole; 4 A molecular sieve; pyridinium chlorochromate; trifluoroacetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(00)86320-X