(4S,6S,7S)-(2E,8E,10E,12E)-14-(benzyloxy)-7-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

Base Information

Chemical Name:(4S,6S,7S)-(2E,8E,10E,12E)-14-(benzyloxy)-7-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate
CAS No.:112505-68-7
Molecular Formula:C₂₇H₃₈O₄
Molecular Weight:426.596
Hs Code.:

Synonyms:(4S,6S,7S)-(2E,8E,10E,12E)-14-(benzyloxy)-7-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

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Chemical Property of (4S,6S,7S)-(2E,8E,10E,12E)-14-(benzyloxy)-7-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

Chemical Property:

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Technology Process of (4S,6S,7S)-(2E,8E,10E,12E)-14-(benzyloxy)-7-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

There total 10 articles about (4S,6S,7S)-(2E,8E,10E,12E)-14-(benzyloxy)-7-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate 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:

: 101376-74-3
(E)-4-(benzyloxy)-2-methylbut-2-enal

: 112505-68-7
(4S,6S,7S)-(2E,8E,10E,12E)-14-(benzyloxy)-7-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, RT, 10 min, 2.) RT, 30 min

2: 88 percent / i-Bu₂AlH / diethyl ether; hexane / 0.33 h / -70 °C

3: 14.58 g / NBS, dimethyl sulfide / CH₂Cl₂ / 1 h

4: 84 percent / 0.58 h / 100 °C

5: t-BuOK / tetrahydrofuran / 0.75 h / -78 - -45 °C

6: aq. AcOH / tetrahydrofuran / 1.17 h / 60 - 65 °C

7: acetonitrile / 16 h / 80 - 85 °C

With N-Bromosuccinimide; dimethylsulfide; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo00240a032

Reference yield:

: 79646-66-5
(2S,3S,5S,6R)-2-methoxy-3,5-dimethyltetrahydropyran-6-methanol

: 112505-68-7
(4S,6S,7S)-(2E,8E,10E,12E)-14-(benzyloxy)-7-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) DMSO/oxalyl chloride, 2.) Et₃N / 1.) CH₂Cl₂, from -60 to -30 deg C, 28 min, 2.) RT, 30 min

2: t-BuOK / tetrahydrofuran / 0.75 h / -78 - -45 °C

3: aq. AcOH / tetrahydrofuran / 1.17 h / 60 - 65 °C

4: acetonitrile / 16 h / 80 - 85 °C

With oxalyl dichloride; potassium tert-butylate; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; acetonitrile;
DOI:10.1021/jo00240a032

Reference yield:

: 110715-33-8
(2S,3S,5S,6R)-2-methoxy-3,5-dimethyltetrahydropyran-6-carboxaldehyde

: 112505-68-7
(4S,6S,7S)-(2E,8E,10E,12E)-14-(benzyloxy)-7-hydroxy-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

Guidance literature:: Multi-step reaction with 3 steps

1: t-BuOK / tetrahydrofuran / 0.75 h / -78 - -45 °C

2: aq. AcOH / tetrahydrofuran / 1.17 h / 60 - 65 °C

3: acetonitrile / 16 h / 80 - 85 °C

With potassium tert-butylate; acetic acid; In tetrahydrofuran; acetonitrile;
DOI:10.1021/jo00240a032