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

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Chemical Name:Benzoic acid (3R,4S)-4-benzyloxymethoxy-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-5-enyl ester
CAS No.:134744-39-1
Molecular Formula:C₂₈H₄₀O₅Si
Molecular Weight:484.708
Hs Code.:

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

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

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

There total 15 articles about Benzoic acid (3R,4S)-4-benzyloxymethoxy-3-(tert-butyl-dimethyl-silanyloxy)-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: 90.0%

: 3587-60-8
Benzyloxymethyl chloride

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

: 134744-39-1
Benzoic acid (3R,4S)-4-benzyloxymethoxy-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-5-enyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; at 25 ℃;
DOI:10.1016/S0040-4020(01)96139-3

Reference yield:

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

: 134744-39-1
Benzoic acid (3R,4S)-4-benzyloxymethoxy-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-5-enyl ester

Guidance literature:: Multi-step reaction with 8 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

8: 90 percent / iPr₂NEt / 25 °C

With pyridine; 1H-imidazole; N-Bromosuccinimide; lithium aluminium tetrahydride; phthalic acid dimethyl ester; camphor-10-sulfonic acid; N-ethyl-N,N-diisopropylamine; 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

: 134744-39-1
Benzoic acid (3R,4S)-4-benzyloxymethoxy-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-5-enyl ester

Guidance literature:: Multi-step reaction with 6 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

6: 90 percent / iPr₂NEt / 25 °C

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