(2R,3S,4R,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol

Base Information

Chemical Name:(2R,3S,4R,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol
CAS No.:1356828-74-4
Molecular Formula:C₁₅H₂₀O₅
Molecular Weight:280.321
Hs Code.:

Synonyms:(2R,3S,4R,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol

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Chemical Property of (2R,3S,4R,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol

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Technology Process of (2R,3S,4R,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol

There total 14 articles about (2R,3S,4R,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol 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:

: (2-methoxy-6-((E)-2-((3aR,4R,6R,6aS)-2,2,6-trimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)vinyl)phenyl)methanol

: 1356828-74-4
(2R,3S,4R,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 3h;
DOI:10.1016/j.tet.2011.12.008

Reference yield:

: C₁₈H₂₄O₅

: 1356828-74-4
(2R,3S,4R,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 5h;
DOI:10.3998/ark.5550190.0013.633

Reference yield:

: 76222-68-9
((3aR,4R,6R,6aS)-2,2,6-trimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

: 1356828-74-4
(2R,3S,4R,5R,E)-2-(2-(hydroxymethyl)-3-methoxystyryl)-5-methyl-tetrahydrofuran-3,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / -78 - 20 °C

2: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / Reflux

4: diisobutylaluminium hydride / dichloromethane; toluene / 2.08 h / -78 °C

5: hydrogenchloride / tetrahydrofuran; water / 3 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; hydrogenchloride; oxalyl dichloride; potassium tert-butylate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 1: Swern oxidation / 2: Wittig homologation;
DOI:10.1016/j.tet.2011.12.008