erythro-9,14-dihydroxy-10-(1,2-dihydroxy-2-methylpropyl)-1-(phenylthio)-3,7,13-trimethyltetradeca-(E,E,E)-2,6,12-triene

Base Information

Chemical Name:erythro-9,14-dihydroxy-10-(1,2-dihydroxy-2-methylpropyl)-1-(phenylthio)-3,7,13-trimethyltetradeca-(E,E,E)-2,6,12-triene
CAS No.:97634-60-1
Molecular Formula:C₂₇H₄₂O₄S
Molecular Weight:462.694
Hs Code.:

Synonyms:erythro-9,14-dihydroxy-10-(1,2-dihydroxy-2-methylpropyl)-1-(phenylthio)-3,7,13-trimethyltetradeca-(E,E,E)-2,6,12-triene

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Chemical Property of erythro-9,14-dihydroxy-10-(1,2-dihydroxy-2-methylpropyl)-1-(phenylthio)-3,7,13-trimethyltetradeca-(E,E,E)-2,6,12-triene

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Technology Process of erythro-9,14-dihydroxy-10-(1,2-dihydroxy-2-methylpropyl)-1-(phenylthio)-3,7,13-trimethyltetradeca-(E,E,E)-2,6,12-triene

There total 18 articles about erythro-9,14-dihydroxy-10-(1,2-dihydroxy-2-methylpropyl)-1-(phenylthio)-3,7,13-trimethyltetradeca-(E,E,E)-2,6,12-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: 61.0%

: 97644-30-9
erythro-9-hydroxy-10-<1-oxo-2-methyl-2-(trimethylsiloxy)propyl>-1-(phenylthio)-14-(trimethylsiloxy)-3,7,13-trimethyltetradeca-(E,E,E)-2,6,12-triene

: 97634-60-1
erythro-9,14-dihydroxy-10-(1,2-dihydroxy-2-methylpropyl)-1-(phenylthio)-3,7,13-trimethyltetradeca-(E,E,E)-2,6,12-triene

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at -20 ℃; for 2h;
DOI:10.1021/jo00220a018

Reference yield:

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

: 97634-60-1
erythro-9,14-dihydroxy-10-(1,2-dihydroxy-2-methylpropyl)-1-(phenylthio)-3,7,13-trimethyltetradeca-(E,E,E)-2,6,12-triene

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) selenium dioxide, benzoic acid, 70percent tert-butyl hydroperoxide, 2.) dimethyl sulfide / 1.) CH₂Cl₂, RT, 26 h, 2.) reflux, 6 h

2: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -70 deg C, 1 h, 2.) CH₂Cl₂, RT, overnight

3: 1.) butyllithium / 1.) THF, hexane, HMPA, 0 deg C, 55 min, 2.) THF, hexane, HMPA, RT, 3 h

4: 97 percent / 1M sodium hydroxide / methanol; H₂O / 3 h / Ambient temperature

5: 1.) 2,2'-bipyridine, butyllithium / 1.) THF, hexane, -60 deg C, 2.) THF, hexane, RT, 2.5 h

6: 1.) BuLi, 2,2'-bipyridine / 1.) THF, -60 deg C, 2.) 2.5 h

7: 1.) borane-THF complex, 2-methyl-2-butene, 2.) 3 M aq. sodium hydroxide, 30percent hydrogen peroxide / 1a.) THF, 0 deg C, 2.5 h, 2.b.) THF, RT, overnight, 2.) THF, RT, 3 h

8: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, from -15 deg C to -10 deg C, 15 min, 2.) CH₂Cl₂, -10 deg C, 15 min

9: 1.) 0.5 M lithium diisopropylamide / 1.) THF, hexane, -78 deg C, 1 h, 2.) 30 s

10: 61 percent / LiAlH₄ / diethyl ether / 2 h / -20 °C

With tert.-butylhydroperoxide; [2,2]bipyridinyl; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; selenium(IV) oxide; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; dimethylsulfide; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; benzoic acid; lithium diisopropyl amide; In methanol; diethyl ether; water;
DOI:10.1021/jo00220a018

Reference yield:

: 764-32-9
5-methyl-4-hexenal

: 97634-60-1
erythro-9,14-dihydroxy-10-(1,2-dihydroxy-2-methylpropyl)-1-(phenylthio)-3,7,13-trimethyltetradeca-(E,E,E)-2,6,12-triene

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) NaH / 1.) glyme, 0 deg C, 3h, 2.) 18 h

2: 94 percent / LiAlH₄ / diethyl ether / 20 h / Ambient temperature

3: 91 percent / pyridine / 24 h / Ambient temperature

4: 1.) m-chloroperoxybenzoic acid, 2.) water, perchloric acid / 1.) THF, a) 0 deg C, 30 min, b) RT, 30 min, 2.) THF, RT, 30 min

5: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, RT, 3.5 h

6: 84 percent / barium hydroxide / methanol / 0.17 h

7: 85 percent / 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

8: 1.) 0.5 M lithium diisopropylamide / 1.) THF, hexane, -78 deg C, 1 h, 2.) 30 s

9: 61 percent / LiAlH₄ / diethyl ether / 2 h / -20 °C

With pyridine; dmap; barium dihydroxide; lithium aluminium tetrahydride; perchloric acid; oxalyl dichloride; water; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane;
DOI:10.1021/jo00220a018