(2R,3R,4S,5S)-2-(2-(hydroxymethyl)styryl)-5-methyltetrahydrofuran-3,4-diol

Base Information

Chemical Name:(2R,3R,4S,5S)-2-(2-(hydroxymethyl)styryl)-5-methyltetrahydrofuran-3,4-diol
CAS No.:1392482-53-9
Molecular Formula:C₁₄H₁₈O₄
Molecular Weight:250.295
Hs Code.:

Synonyms:(2R,3R,4S,5S)-2-(2-(hydroxymethyl)styryl)-5-methyltetrahydrofuran-3,4-diol

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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,4S,5S)-2-(2-(hydroxymethyl)styryl)-5-methyltetrahydrofuran-3,4-diol

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Technology Process of (2R,3R,4S,5S)-2-(2-(hydroxymethyl)styryl)-5-methyltetrahydrofuran-3,4-diol

There total 7 articles about (2R,3R,4S,5S)-2-(2-(hydroxymethyl)styryl)-5-methyltetrahydrofuran-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: 69.0%

: 1392482-46-0
tert-butyldimethyl(2-((E)-2-((3aS,4R,6S,6aR)-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]-dioxol-4-yl)vinyl)benzyl-oxy)silane

: 1392482-53-9
(2R,3R,4S,5S)-2-(2-(hydroxymethyl)styryl)-5-methyltetrahydrofuran-3,4-diol

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 18h; Inert atmosphere;
DOI:10.1039/c2ob25069a

Reference yield:

: 1043926-97-1
2-(tert-butyldimethylsilyloxymethyl)benzyl chloride

: 1392482-53-9
(2R,3R,4S,5S)-2-(2-(hydroxymethyl)styryl)-5-methyltetrahydrofuran-3,4-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 5 h / 155 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / 0 °C / Inert atmosphere

2.2: 8 h / 0 - 50 °C / Inert atmosphere

3.1: hydrogenchloride / tetrahydrofuran; water / 18 h / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; water; 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1039/c2ob25069a

Reference yield:

: 1392482-39-1
(3aS,4R,6S,6aR)-4-(benzyloxymethyl)-2,2,6-trimethyltetrahydrofuro-[3,4-d][1,3]dioxole

: 1392482-53-9
(2R,3R,4S,5S)-2-(2-(hydroxymethyl)styryl)-5-methyltetrahydrofuran-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 3 h / 20 °C / 750.08 Torr

2.1: Dess-Martin periodane / dichloromethane / 22 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / 0 °C / Inert atmosphere

3.2: 8 h / 0 - 50 °C / Inert atmosphere

4.1: hydrogenchloride / tetrahydrofuran; water / 18 h / 20 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; palladium 10% on activated carbon; hydrogen; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; water; 3.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1039/c2ob25069a