tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate

Base Information

Chemical Name:tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate
CAS No.:1287228-24-3
Molecular Formula:C₁₈H₂₅NO₄
Molecular Weight:319.401
Hs Code.:

Synonyms:tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate

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Chemical Property of tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate

Chemical Property:

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Technology Process of tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate

There total 4 articles about tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate 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: 81.0%

: 1287228-22-1
(4S,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate

: 1287228-24-3
tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate

: 1287228-23-2
tert-butyl ((3S,4R,5R)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; at 55 ℃; for 16h; stereoselective reaction; Inert atmosphere;
DOI:10.1039/c0ob00643b

Reference yield:

: 1287228-19-6
(S)-tert-butyl 4-((S,Z)-1-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 1287228-24-3
tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate

Guidance literature:: Multi-step reaction with 4 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

3: iron(III) chloride adsorbed on silica gel / chloroform / 12 h / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine / tetrahydrofuran / 16 h / 55 °C / Inert atmosphere

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iron(III) chloride adsorbed on silica gel; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1039/c0ob00643b

Reference yield:

: 1287228-20-9
(S)-tert-butyl 4-((S,Z)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

: 1287228-24-3
tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate

Guidance literature:: Multi-step reaction with 3 steps

1: dmap; triethylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

2: iron(III) chloride adsorbed on silica gel / chloroform / 12 h / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine / tetrahydrofuran / 16 h / 55 °C / Inert atmosphere

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; iron(III) chloride adsorbed on silica gel; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; chloroform;
DOI:10.1039/c0ob00643b