(2R,3R,5R)-5-allyl-2-((S)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydrofuran

Base Information

Chemical Name:(2R,3R,5R)-5-allyl-2-((S)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydrofuran
CAS No.:1309924-64-8
Molecular Formula:C₁₈H₂₆O₂
Molecular Weight:274.403
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,5R)-5-allyl-2-((S)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydrofuran

Chemical Property:

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Technology Process of (2R,3R,5R)-5-allyl-2-((S)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydrofuran

There total 6 articles about (2R,3R,5R)-5-allyl-2-((S)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydrofuran 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:

: 1309924-61-5
(2R,3R)-2-((S)-1-(benzyloxy)propan-2-yl)-5-ethoxy-3-methyltetrahydrofuran

: 762-72-1
allyl-trimethyl-silane

: 1309924-64-8
(2R,3R,5R)-5-allyl-2-((S)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydrofuran

: (2R,3R,5S)-5-allyl-2-((S)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydrofuran

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -84 ℃; for 2h; optical yield given as %de; Inert atmosphere;
DOI:10.1039/c1ob05240c

Reference yield:

: 882980-43-0
2-benzyloxy-1-methylpyridinium triflate

: 1309924-64-8
(2R,3R,5R)-5-allyl-2-((S)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydrofuran

: (2R,3R,5S)-5-allyl-2-((S)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydrofuran

Guidance literature:: Multi-step reaction with 6 steps

1: magnesium oxide / 1,2-dichloro-ethane / 15 h / Reflux; Inert atmosphere

2: diisobutylaluminium hydride / diethyl ether; toluene / 0.3 h / -110 °C / Inert atmosphere

3: tetrahydrofuran; diethyl ether / -80 °C / Inert atmosphere

4: triethylamine / dichloromethane / 25 °C / Inert atmosphere

5: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 3 h / Reflux; Inert atmosphere

6: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -84 °C / Inert atmosphere

With 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; magnesium oxide; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; toluene; benzene; 5: Ueno-Stork reaction;
DOI:10.1039/c1ob05240c

Reference yield:

: 1309924-60-4
(((2S,3R)-3-(2-bromo-1-ethoxyethoxy)-2-methylpent-4-enyloxy)methyl)benzene

: 1309924-64-8
(2R,3R,5R)-5-allyl-2-((S)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydrofuran

: (2R,3R,5S)-5-allyl-2-((S)-1-(benzyloxy)propan-2-yl)-3-methyltetrahydrofuran

Guidance literature:: Multi-step reaction with 2 steps

1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 3 h / Reflux; Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -84 °C / Inert atmosphere

With 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tri-n-butyl-tin hydride; In dichloromethane; benzene; 1: Ueno-Stork reaction;
DOI:10.1039/c1ob05240c