(2S,3S,5S)-6-<(1E,3E,5E)-7-(benzyloxy)-5-methyl-1,3,5-heptatrienyl>-2-methoxy-3,5-dimethyltetrahydropyran

Base Information

Chemical Name:(2S,3S,5S)-6-<(1E,3E,5E)-7-(benzyloxy)-5-methyl-1,3,5-heptatrienyl>-2-methoxy-3,5-dimethyltetrahydropyran
CAS No.:112505-66-5
Molecular Formula:C₂₃H₃₂O₃
Molecular Weight:356.505
Hs Code.:

Synonyms:(2S,3S,5S)-6-<(1E,3E,5E)-7-(benzyloxy)-5-methyl-1,3,5-heptatrienyl>-2-methoxy-3,5-dimethyltetrahydropyran

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Chemical Property of (2S,3S,5S)-6-<(1E,3E,5E)-7-(benzyloxy)-5-methyl-1,3,5-heptatrienyl>-2-methoxy-3,5-dimethyltetrahydropyran

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Technology Process of (2S,3S,5S)-6-<(1E,3E,5E)-7-(benzyloxy)-5-methyl-1,3,5-heptatrienyl>-2-methoxy-3,5-dimethyltetrahydropyran

There total 7 articles about (2S,3S,5S)-6-<(1E,3E,5E)-7-(benzyloxy)-5-methyl-1,3,5-heptatrienyl>-2-methoxy-3,5-dimethyltetrahydropyran 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:

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

: 112505-65-4
diethyl (2E,4E)-<6-(benzyloxy)-4-methyl-2,4-hexadienyl>phosphonate

: 112505-66-5
(2S,3S,5S)-6-<(1E,3E,5E)-7-(benzyloxy)-5-methyl-1,3,5-heptatrienyl>-2-methoxy-3,5-dimethyltetrahydropyran

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at -78 - -45 ℃; for 0.75h;
DOI:10.1021/jo00240a032

Reference yield:

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

: 112505-66-5
(2S,3S,5S)-6-<(1E,3E,5E)-7-(benzyloxy)-5-methyl-1,3,5-heptatrienyl>-2-methoxy-3,5-dimethyltetrahydropyran

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

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

: 112505-66-5
(2S,3S,5S)-6-<(1E,3E,5E)-7-(benzyloxy)-5-methyl-1,3,5-heptatrienyl>-2-methoxy-3,5-dimethyltetrahydropyran

Guidance literature:: Multi-step reaction with 2 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

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