(3R,6E)-3-(Benzyloxy)-2,6-dimethyl-8-(phenylthio)-6-octene-2-ol

Base Information

Chemical Name:(3R,6E)-3-(Benzyloxy)-2,6-dimethyl-8-(phenylthio)-6-octene-2-ol
CAS No.:119840-69-6
Molecular Formula:C₂₃H₃₀O₂S
Molecular Weight:370.556
Hs Code.:

Synonyms:

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Chemical Property of (3R,6E)-3-(Benzyloxy)-2,6-dimethyl-8-(phenylthio)-6-octene-2-ol

Chemical Property:

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Technology Process of (3R,6E)-3-(Benzyloxy)-2,6-dimethyl-8-(phenylthio)-6-octene-2-ol

There total 11 articles about (3R,6E)-3-(Benzyloxy)-2,6-dimethyl-8-(phenylthio)-6-octene-2-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:

: 105-87-3,8022-83-1
3,7-dimethyl-2E,6-octadien-1-yl acetate

: 119840-69-6
(3R,6E)-3-(Benzyloxy)-2,6-dimethyl-8-(phenylthio)-6-octene-2-ol

Guidance literature:: Multi-step reaction with 11 steps

1: SeO₂ / ethanol / 3 h / Heating

2: 2 percent / NaBH₄ / diethyl ether; ethanol / 30 h / 0 °C

3: 79 percent / D-(-)-diisopropyl tartrate (D-(-)-DIPT), Ti(Oi-Pr)4, tert.-butyl hydroperoxide (TBHP) / CH₂Cl₂ / 4 h / -20 °C

5: 85 percent / 18 M H₂SO₄ / tetrahydrofuran; H₂O / 30 h / 0 °C

6: 96 percent / p-toluenesulfonic acid / 2 h / Ambient temperature

7: 93 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

8: CCl₄, PPh₃ / benzene / 24 h / Heating

9: dimethylformamide / 0.5 h / 0 °C

10: 91 percent / 1 M aq. HCl / methanol / 12 h / Ambient temperature

11: 1) NaH / 1) DMF, 0 deg C, 15 min, 2) room temp., 12 h

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; tetrachloromethane; sodium tetrahydroborate; selenium(IV) oxide; sulfuric acid; sodium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00304a022

Reference yield:

: 37905-03-6
8-hydroxygeranyl acetate

: 119840-69-6
(3R,6E)-3-(Benzyloxy)-2,6-dimethyl-8-(phenylthio)-6-octene-2-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 79 percent / D-(-)-diisopropyl tartrate (D-(-)-DIPT), Ti(Oi-Pr)4, tert.-butyl hydroperoxide (TBHP) / CH₂Cl₂ / 4 h / -20 °C

3: 85 percent / 18 M H₂SO₄ / tetrahydrofuran; H₂O / 30 h / 0 °C

4: 96 percent / p-toluenesulfonic acid / 2 h / Ambient temperature

5: 93 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

6: CCl₄, PPh₃ / benzene / 24 h / Heating

7: dimethylformamide / 0.5 h / 0 °C

8: 91 percent / 1 M aq. HCl / methanol / 12 h / Ambient temperature

9: 1) NaH / 1) DMF, 0 deg C, 15 min, 2) room temp., 12 h

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; tetrachloromethane; sulfuric acid; sodium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00304a022

Reference yield:

: 37905-02-5
(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate

: 119840-69-6
(3R,6E)-3-(Benzyloxy)-2,6-dimethyl-8-(phenylthio)-6-octene-2-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 2 percent / NaBH₄ / diethyl ether; ethanol / 30 h / 0 °C

2: 79 percent / D-(-)-diisopropyl tartrate (D-(-)-DIPT), Ti(Oi-Pr)4, tert.-butyl hydroperoxide (TBHP) / CH₂Cl₂ / 4 h / -20 °C

4: 85 percent / 18 M H₂SO₄ / tetrahydrofuran; H₂O / 30 h / 0 °C

5: 96 percent / p-toluenesulfonic acid / 2 h / Ambient temperature

6: 93 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

7: CCl₄, PPh₃ / benzene / 24 h / Heating

8: dimethylformamide / 0.5 h / 0 °C

9: 91 percent / 1 M aq. HCl / methanol / 12 h / Ambient temperature

10: 1) NaH / 1) DMF, 0 deg C, 15 min, 2) room temp., 12 h

With titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; tetrachloromethane; sodium tetrahydroborate; sulfuric acid; sodium hydride; potassium carbonate; D-(-)-diisopropyl tartrate; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00304a022