(3R,4S,5R)-3,4-dibenzyloxy-2,4-dimethylhept-1-en-5-ol

Base Information

Chemical Name:(3R,4S,5R)-3,4-dibenzyloxy-2,4-dimethylhept-1-en-5-ol
CAS No.:548487-97-4
Molecular Formula:C₂₃H₃₀O₃
Molecular Weight:354.489
Hs Code.:

Synonyms:(3R,4S,5R)-3,4-dibenzyloxy-2,4-dimethylhept-1-en-5-ol

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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 (3R,4S,5R)-3,4-dibenzyloxy-2,4-dimethylhept-1-en-5-ol

Chemical Property:

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Technology Process of (3R,4S,5R)-3,4-dibenzyloxy-2,4-dimethylhept-1-en-5-ol

There total 9 articles about (3R,4S,5R)-3,4-dibenzyloxy-2,4-dimethylhept-1-en-5-ol 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: 95.0%

: 548487-96-3
(2S,3S,4S,5S)-3,4-dibenzyloxy-2,4-dimethyl-5-ethyl-2-iodomethyltetrahydrofuran

: 548487-97-4
(3R,4S,5R)-3,4-dibenzyloxy-2,4-dimethylhept-1-en-5-ol

Guidance literature:: With acetic acid; zinc; In methanol; diethyl ether; at 23 ℃; for 12h;
DOI:10.1021/ja034865z

Reference yield:

: 548488-20-6
(2S,3S,4S,5S)-4-dimethylphenylsilyl-3-hydroxy-2-hydroxymethyl-2,4-dimethyl-5-ethyltetrahydrofuran

: 548487-97-4
(3R,4S,5R)-3,4-dibenzyloxy-2,4-dimethylhept-1-en-5-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 96 percent / n-Bu₄NI / hexane; dimethylformamide / 12 h / 0 - 23 °C

2.1: 85 percent / cumene hydroperoxide; KH; NMP / n-Bu₄NF / tetrahydrofuran / 40 h / 23 °C

3.1: 98 percent / H₂ / Pd/C / ethanol / 24 h / 760 Torr

4.1: 96 percent / imidazole / dimethylformamide / 12 h / 23 °C

5.1: NaH / dimethylformamide / 0.5 h / 0 °C

5.2: 96 percent / n-Bu₄NI / dimethylformamide / 12 h / 0 - 23 °C

6.1: 97 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 23 °C

7.1: 65 percent / Ph₃P; imidazole; I₂ / benzene / 0.5 h / Heating

8.1: 95 percent / Zn; AcOH / diethyl ether; methanol / 12 h / 23 °C

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; Cumene hydroperoxide; tetrabutyl ammonium fluoride; hydrogen; iodine; potassium hydride; sodium hydride; acetic acid; triphenylphosphine; zinc; palladium on activated charcoal; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja034865z

Reference yield:

: 548487-91-8
(2S,3S,4S,5S)-3-benzyloxy-2-benzyloxymethyl-2,4-dimethyl-5-ethyl-4-hydroxytetrahydrofuran

: 548487-97-4
(3R,4S,5R)-3,4-dibenzyloxy-2,4-dimethylhept-1-en-5-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / H₂ / Pd/C / ethanol / 24 h / 760 Torr

2.1: 96 percent / imidazole / dimethylformamide / 12 h / 23 °C

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 96 percent / n-Bu₄NI / dimethylformamide / 12 h / 0 - 23 °C

4.1: 97 percent / n-Bu₄NF / tetrahydrofuran / 12 h / 23 °C

5.1: 65 percent / Ph₃P; imidazole; I₂ / benzene / 0.5 h / Heating

6.1: 95 percent / Zn; AcOH / diethyl ether; methanol / 12 h / 23 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydride; acetic acid; triphenylphosphine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja034865z