(10E,14E)-(6R,7S)-16-(benzyloxy)-6-(methoxymethoxy)-2,6,10,15-tetramethylhexadeca-2,10,14-trien-7-ol

Base Information

Chemical Name:(10E,14E)-(6R,7S)-16-(benzyloxy)-6-(methoxymethoxy)-2,6,10,15-tetramethylhexadeca-2,10,14-trien-7-ol
CAS No.:132298-89-6
Molecular Formula:C₂₉H₄₆O₄
Molecular Weight:458.682
Hs Code.:

Synonyms:(10E,14E)-(6R,7S)-16-(benzyloxy)-6-(methoxymethoxy)-2,6,10,15-tetramethylhexadeca-2,10,14-trien-7-ol

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Chemical Property of (10E,14E)-(6R,7S)-16-(benzyloxy)-6-(methoxymethoxy)-2,6,10,15-tetramethylhexadeca-2,10,14-trien-7-ol

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Technology Process of (10E,14E)-(6R,7S)-16-(benzyloxy)-6-(methoxymethoxy)-2,6,10,15-tetramethylhexadeca-2,10,14-trien-7-ol

There total 15 articles about (10E,14E)-(6R,7S)-16-(benzyloxy)-6-(methoxymethoxy)-2,6,10,15-tetramethylhexadeca-2,10,14-trien-7-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:

: 82188-73-6
(2S,3S)-2,3-epoxygeraniol

: 132298-89-6
(10E,14E)-(6R,7S)-16-(benzyloxy)-6-(methoxymethoxy)-2,6,10,15-tetramethylhexadeca-2,10,14-trien-7-ol

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / 24 h / 0 °C

2: pTsOH*H₂O / acetonitrile; H₂O / 24 h / 50 °C

3: 73 percent / K₂CO₃ / methanol / 0.67 h / -10 °C

4: 89 percent / i-Pr₂NEt, DMAP / CH₂Cl₂ / 36 h / Ambient temperature

5: 1) BuLi, TMEDA, 2) metallic Na / 1) THF, -78 deg C, 10 min, 2) THF, 2-propanol, 5 h, reflux

With pyridine; dmap; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00007a013

Reference yield:

: 106-24-1
Geraniol

: 132298-89-6
(10E,14E)-(6R,7S)-16-(benzyloxy)-6-(methoxymethoxy)-2,6,10,15-tetramethylhexadeca-2,10,14-trien-7-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / Ti(O-iPr)4, TBHP, L-(+)-DIPT, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / -23 °C

2: pyridine / CH₂Cl₂ / 24 h / 0 °C

3: pTsOH*H₂O / acetonitrile; H₂O / 24 h / 50 °C

4: 73 percent / K₂CO₃ / methanol / 0.67 h / -10 °C

5: 89 percent / i-Pr₂NEt, DMAP / CH₂Cl₂ / 36 h / Ambient temperature

6: 1) BuLi, TMEDA, 2) metallic Na / 1) THF, -78 deg C, 10 min, 2) THF, 2-propanol, 5 h, reflux

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; n-butyllithium; L-(+)-diisopropyl tartrate; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; sodium; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo00007a013

Reference yield:

: 109307-91-7
2-methyl-6-(phenylmethoxy)-2(E)-hexen-1-ol

: 132298-89-6
(10E,14E)-(6R,7S)-16-(benzyloxy)-6-(methoxymethoxy)-2,6,10,15-tetramethylhexadeca-2,10,14-trien-7-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 94 percent / pTsOH / CH₂Cl₂ / 1 h / 0 °C

2: 97 percent / Li, liquid NH₃ / diethyl ether / 0.67 h / -78 °C

3: NaOAc, PCC / CH₂Cl₂ / 1 h / Ambient temperature

4: tetrahydrofuran / 0.67 h / 0 °C

5: 81 percent / DIBAH / hexane / 0.08 h / -78 °C

6: 1) NaH / 1) DMF, 0 deg C, 30 min, 2) room temp., 36 h

7: 91 percent / TsOH*H₂O / methanol / 2 h / Ambient temperature

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

9: dimethylformamide / 1 h / 0 °C

10: 1) BuLi, TMEDA, 2) metallic Na / 1) THF, -78 deg C, 10 min, 2) THF, 2-propanol, 5 h, reflux

With tetrachloromethane; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; ammonia; sodium acetate; sodium; lithium; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00007a013