(2S,3R,6S)-3-Benzyloxy-3-ethyl-6-<(1E)-2-(4-methoxyphenyl)ethenyl>-2-methyltetrahydropyran

Base Information

Chemical Name:(2S,3R,6S)-3-Benzyloxy-3-ethyl-6-<(1E)-2-(4-methoxyphenyl)ethenyl>-2-methyltetrahydropyran
CAS No.:128531-44-2
Molecular Formula:C₂₄H₃₀O₃
Molecular Weight:366.5
Hs Code.:

Synonyms:(2S,3R,6S)-3-Benzyloxy-3-ethyl-6-<(1E)-2-(4-methoxyphenyl)ethenyl>-2-methyltetrahydropyran

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Chemical Property of (2S,3R,6S)-3-Benzyloxy-3-ethyl-6-<(1E)-2-(4-methoxyphenyl)ethenyl>-2-methyltetrahydropyran

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Technology Process of (2S,3R,6S)-3-Benzyloxy-3-ethyl-6-<(1E)-2-(4-methoxyphenyl)ethenyl>-2-methyltetrahydropyran

There total 12 articles about (2S,3R,6S)-3-Benzyloxy-3-ethyl-6-<(1E)-2-(4-methoxyphenyl)ethenyl>-2-methyltetrahydropyran 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: 74.0%

: (1RS,2E,6R,7S)-6-Benzyloxy-6-ethyl-1-(4-methoxyphenyl)-oct-2-en-1,7-diol

: 128531-44-2
(2S,3R,6S)-3-Benzyloxy-3-ethyl-6-<(1E)-2-(4-methoxyphenyl)ethenyl>-2-methyltetrahydropyran

: 128531-45-3
(2S,3R,6R)-3-Benzyloxy-3-ethyl-6-<(1E)-2-(4-methoxyphenyl)ethenyl>-2-methyltetrahydropyran

Guidance literature:: zinc dibromide; In dichloromethane; at -20 ℃; for 1.5h;
DOI:10.1016/S0040-4020(01)87184-2

Reference yield:

: 151255-09-3
(2S,3R)-3-Benzyloxy-3-ethylhept-6-en-2-ol

: 128531-44-2
(2S,3R,6S)-3-Benzyloxy-3-ethyl-6-<(1E)-2-(4-methoxyphenyl)ethenyl>-2-methyltetrahydropyran

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / imidazole / dimethylformamide / 6 h / 80 °C

2: 1) N-methylmorpholine oxide, OsO₄, 2) Na₂S₂O₄, Celite / 1) acetone, H₂O, 6 h, r.t., 2) H₂O, overnight

3: 89 percent / NaIO₄ / methanol; H₂O / 0.5 h / Ambient temperature

4: 1) NaH / 1) THF, 20 min, r.t., 2) THF, 6 h, r.t.

5: 99 percent / NaBH₄, CeCl₃ / methanol / 0.17 h / 0 °C

6: 100 percent / n-Bu₄NF / tetrahydrofuran / 7 h / 60 °C

7: 5.4 percent / ZnBr₂ / CH₂Cl₂ / 1.5 h / -20 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium dithionite; cerium(III) chloride; Celite; tetrabutyl ammonium fluoride; sodium hydride; 4-methylmorpholine N-oxide; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)87184-2

Reference yield:

: (2S,3RS)-2-Benzyloxymethoxyhept-6-en-3-ol

: 128531-44-2
(2S,3R,6S)-3-Benzyloxy-3-ethyl-6-<(1E)-2-(4-methoxyphenyl)ethenyl>-2-methyltetrahydropyran

Guidance literature:: Multi-step reaction with 11 steps

1: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 to -50 deg C, 1.5 h, 2) 2 h

2: 1) Mg / 1) THF, 2) THF, -78 deg C

3: 1) NaH / 1) DMF, 2 h, r.t., 2) 2 h, r.t.

4: 75 percent / 4N HCl / methanol / 4 h / 50 °C

5: 100 percent / imidazole / dimethylformamide / 6 h / 80 °C

6: 1) N-methylmorpholine oxide, OsO₄, 2) Na₂S₂O₄, Celite / 1) acetone, H₂O, 6 h, r.t., 2) H₂O, overnight

7: 89 percent / NaIO₄ / methanol; H₂O / 0.5 h / Ambient temperature

8: 1) NaH / 1) THF, 20 min, r.t., 2) THF, 6 h, r.t.

9: 99 percent / NaBH₄, CeCl₃ / methanol / 0.17 h / 0 °C

10: 100 percent / n-Bu₄NF / tetrahydrofuran / 7 h / 60 °C

11: 5.4 percent / ZnBr₂ / CH₂Cl₂ / 1.5 h / -20 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; sodium dithionite; cerium(III) chloride; oxalyl dichloride; Celite; tetrabutyl ammonium fluoride; sodium hydride; magnesium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)87184-2