(4E,6E,10R)-10-hydroxy-1-(4-methoxybenzyl)oxy-7-methyltrideca-4,6,12-triene

Base Information

Chemical Name:(4E,6E,10R)-10-hydroxy-1-(4-methoxybenzyl)oxy-7-methyltrideca-4,6,12-triene
CAS No.:179618-63-4
Molecular Formula:C₂₂H₃₂O₃
Molecular Weight:344.494
Hs Code.:

Synonyms:(4E,6E,10R)-10-hydroxy-1-(4-methoxybenzyl)oxy-7-methyltrideca-4,6,12-triene

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Chemical Property of (4E,6E,10R)-10-hydroxy-1-(4-methoxybenzyl)oxy-7-methyltrideca-4,6,12-triene

Chemical Property:

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Technology Process of (4E,6E,10R)-10-hydroxy-1-(4-methoxybenzyl)oxy-7-methyltrideca-4,6,12-triene

There total 12 articles about (4E,6E,10R)-10-hydroxy-1-(4-methoxybenzyl)oxy-7-methyltrideca-4,6,12-triene 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:

: 106-24-1
Geraniol

: 179618-63-4
(4E,6E,10R)-10-hydroxy-1-(4-methoxybenzyl)oxy-7-methyltrideca-4,6,12-triene

Guidance literature:: Multi-step reaction with 8 steps

1: 39 percent / potassium peroxomonosulfate, KHSO₃ / CH₂Cl₂; acetone; H₂O / 2 h / 0 °C / KH₂PO₄ and Na₂HPO₄ buffer, pH 7.5

2: 67 percent / TsOH*H₂O / H₂O / 2 h

3: CBr₄, PPh₃ / CH₂Cl₂ / 1 h / 0 °C

4: benzene / 2.5 h / Heating

5: t-BuOK / tetrahydrofuran / 1.5 h

6: 99 percent / TsOH*H₂O / methanol; H₂O / 5 h / 20 °C

7: 94 percent / NaIO₄ / acetone; H₂O / 2 h / 20 °C

8: 1.) <(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethoxy)>cyclopentadienyl-chlorotitanium / 1.) THF, 0 deg C, 1 h, 2.) THF, -78 deg C, 1.5 h

With potassium bisulfite; sodium periodate; oxone; carbon tetrabromide; ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethoxy))cyclopentadienyl-chlorotitanium; potassium tert-butylate; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; benzene;
DOI:10.1016/0040-4020(96)00899-X

Reference yield:

: 124150-94-3
(E)-3-methyl-5-(2,2,5,5-tetramethyl-1,3-dioxolan-4-yl)pent-2-en-1-ol

: 179618-63-4
(4E,6E,10R)-10-hydroxy-1-(4-methoxybenzyl)oxy-7-methyltrideca-4,6,12-triene

Guidance literature:: Multi-step reaction with 6 steps

1: CBr₄, PPh₃ / CH₂Cl₂ / 1 h / 0 °C

2: benzene / 2.5 h / Heating

3: t-BuOK / tetrahydrofuran / 1.5 h

4: 99 percent / TsOH*H₂O / methanol; H₂O / 5 h / 20 °C

5: 94 percent / NaIO₄ / acetone; H₂O / 2 h / 20 °C

6: 1.) <(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethoxy)>cyclopentadienyl-chlorotitanium / 1.) THF, 0 deg C, 1 h, 2.) THF, -78 deg C, 1.5 h

With sodium periodate; carbon tetrabromide; ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethoxy))cyclopentadienyl-chlorotitanium; potassium tert-butylate; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; acetone; benzene;
DOI:10.1016/0040-4020(96)00899-X

Reference yield:

: 83324-69-0
(E)-8-bromo-2,3-O-isopropylidene-2,6-dimethyl-6-octene-2,3-diol

: 179618-63-4
(4E,6E,10R)-10-hydroxy-1-(4-methoxybenzyl)oxy-7-methyltrideca-4,6,12-triene

Guidance literature:: Multi-step reaction with 5 steps

1: benzene / 2.5 h / Heating

2: t-BuOK / tetrahydrofuran / 1.5 h

3: 99 percent / TsOH*H₂O / methanol; H₂O / 5 h / 20 °C

4: 94 percent / NaIO₄ / acetone; H₂O / 2 h / 20 °C

5: 1.) <(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethoxy)>cyclopentadienyl-chlorotitanium / 1.) THF, 0 deg C, 1 h, 2.) THF, -78 deg C, 1.5 h

With sodium periodate; ((4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-bis(diphenylmethoxy))cyclopentadienyl-chlorotitanium; potassium tert-butylate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; acetone; benzene;
DOI:10.1016/0040-4020(96)00899-X