Benzoic acid (3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-hex-5-enyl ester

Base Information

Chemical Name:Benzoic acid (3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-hex-5-enyl ester
CAS No.:134744-38-0
Molecular Formula:C₂₀H₃₂O₄Si
Molecular Weight:364.557
Hs Code.:

Synonyms:Benzoic acid (3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-hex-5-enyl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Benzoic acid (3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-hex-5-enyl ester

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Technology Process of Benzoic acid (3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-hex-5-enyl ester

There total 13 articles about Benzoic acid (3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-hex-5-enyl ester 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: 80.0%

: 134776-80-0
Benzoic acid (3R,4S)-3,4-dihydroxy-4-methyl-hex-5-enyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 134744-38-0
Benzoic acid (3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-hex-5-enyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 55 ℃; for 12h;
DOI:10.1016/S0040-4020(01)96139-3

Reference yield:

: (2R,3R,4R)-2-Hydroxymethyl-6-methoxy-3-methyl-tetrahydro-pyran-3,4-diol

: 134744-38-0
Benzoic acid (3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-hex-5-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: DMP, camphorosulfonic acid / 3 h / 25 °C

2: 77 percent / NBS, PPh₃ / hexamethylphosphoric acid triamide / 1 h / 80 °C

3: activated Zn-dust / propan-2-ol; H₂O / Heating

4: LiAlH₄ / diethyl ether / -50 °C

5: pyridine / 1 h / Ambient temperature

6: 83 percent / CF₃COOH / tetrahydrofuran; H₂O / 5 h / 25 °C

7: 80 percent / imidazole / dimethylformamide / 12 h / 55 °C

With pyridine; 1H-imidazole; N-Bromosuccinimide; lithium aluminium tetrahydride; phthalic acid dimethyl ester; camphor-10-sulfonic acid; triphenylphosphine; trifluoroacetic acid; zinc; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1016/S0040-4020(01)96139-3

Reference yield:

: 134744-37-9
(3aR,4S,6S,7aR)-4-Bromomethyl-6-methoxy-2,2,3a-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

: 134744-38-0
Benzoic acid (3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-4-methyl-hex-5-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: activated Zn-dust / propan-2-ol; H₂O / Heating

2: LiAlH₄ / diethyl ether / -50 °C

3: pyridine / 1 h / Ambient temperature

4: 83 percent / CF₃COOH / tetrahydrofuran; H₂O / 5 h / 25 °C

5: 80 percent / imidazole / dimethylformamide / 12 h / 55 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; trifluoroacetic acid; zinc; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1016/S0040-4020(01)96139-3