(E)-(2S,3S,4R,5S)-8-Benzyloxy-3,5-dimethyl-oct-6-ene-2,4-diol

Base Information

Chemical Name:(E)-(2S,3S,4R,5S)-8-Benzyloxy-3,5-dimethyl-oct-6-ene-2,4-diol
CAS No.:121896-50-2
Molecular Formula:C₁₇H₂₆O₃
Molecular Weight:278.392
Hs Code.:

Synonyms:(E)-(2S,3S,4R,5S)-8-Benzyloxy-3,5-dimethyl-oct-6-ene-2,4-diol

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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 (E)-(2S,3S,4R,5S)-8-Benzyloxy-3,5-dimethyl-oct-6-ene-2,4-diol

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Technology Process of (E)-(2S,3S,4R,5S)-8-Benzyloxy-3,5-dimethyl-oct-6-ene-2,4-diol

There total 13 articles about (E)-(2S,3S,4R,5S)-8-Benzyloxy-3,5-dimethyl-oct-6-ene-2,4-diol 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: 79.0%

: (E)-(2R,3R,4S)-7-Benzyloxy-4-methyl-2-(R)-oxiranyl-hept-5-en-3-ol

: 121896-50-2
(E)-(2S,3S,4R,5S)-8-Benzyloxy-3,5-dimethyl-oct-6-ene-2,4-diol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at -30 ℃;
DOI:10.1246/cl.1988.2041

Reference yield:

: 111149-31-6
(3R,4S)-(E)-7-benzyloxy-4-methyl-1-trimethylsilylhept-5-en-1-yn-3-ol

: 121896-50-2
(E)-(2S,3S,4R,5S)-8-Benzyloxy-3,5-dimethyl-oct-6-ene-2,4-diol

Guidance literature:: Multi-step reaction with 10 steps

1: n-Bu₄NF / tetrahydrofuran / Ambient temperature

2: 87 percent / imidazole / dimethylformamide / Ambient temperature

3: 1.)n-BuLi / 1.) THF, -72 deg C; 2.) THF, -45 deg C

4: H₂ / Lindlar catalyst / benzene / Ambient temperature

5: concd. HCl / methanol / Ambient temperature

6: 87 percent / CuI / diethyl ether / 0 °C

7: 42 percent / LDA, MoOPh / tetrahydrofuran / -78 °C

8: 92 percent / Et₃N / CH₂Cl₂ / 0 °C

9: 70 percent / NaBH₄ / ethanol / Ambient temperature

10: 79 percent / LiAlH₄ / tetrahydrofuran / -30 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; MoO₅*pyridine*HMPA; tetrabutyl ammonium fluoride; hydrogen; triethylamine; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1246/cl.1988.2041

Reference yield:

: 120448-41-1
(3R,4S)-(E)-7-benzyloxy-4-methylhept-5-en-1-yn-3-ol

: 121896-50-2
(E)-(2S,3S,4R,5S)-8-Benzyloxy-3,5-dimethyl-oct-6-ene-2,4-diol

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / imidazole / dimethylformamide / Ambient temperature

2: 1.)n-BuLi / 1.) THF, -72 deg C; 2.) THF, -45 deg C

3: H₂ / Lindlar catalyst / benzene / Ambient temperature

4: concd. HCl / methanol / Ambient temperature

5: 87 percent / CuI / diethyl ether / 0 °C

6: 42 percent / LDA, MoOPh / tetrahydrofuran / -78 °C

7: 92 percent / Et₃N / CH₂Cl₂ / 0 °C

8: 70 percent / NaBH₄ / ethanol / Ambient temperature

9: 79 percent / LiAlH₄ / tetrahydrofuran / -30 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; MoO₅*pyridine*HMPA; hydrogen; triethylamine; lithium diisopropyl amide; Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1246/cl.1988.2041