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

Base Information

• Chemical Name: tert-butyl ((3S,4S,5R)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate
• CAS No.: 1011247-70-3
• Molecular Formula: C₁₈H₂₅NO₄
• Molecular Weight: 319.401
• Mol file: 1011247-70-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about tert-butyl ((3S,4S,5R)-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: 59.0%

(4R,5S,Z)-4-(benzyloxy)-5-((tert-butoxycarbonyl)amino)-6-hydroxyhex-2-en-1-yl acetate (1011247-68-9) → tert-butyl ((3S,4S,5S)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate (1011247-72-5) + tert-butyl ((3S,4S,5R)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate (1011247-70-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; at 55 ℃; for 8h; stereoselective reaction; Inert atmosphere;

DOI:10.1039/c0ob00643b

Reference yield:

(S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1011247-64-5) → tert-butyl ((3S,4S,5R)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate (1011247-70-3)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; triethylamine / dichloromethane / 0.17 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 / 8 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

Reference yield:

(S)-tert-butyl 4-((R,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate (1011247-66-7) → tert-butyl ((3S,4S,5R)-4-(benzyloxy)-5-vinyltetrahydrofuran-3-yl)carbamate (1011247-70-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine / tetrahydrofuran / 8 h / 55 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; iron(III) chloride adsorbed on silica gel; triphenylphosphine; In tetrahydrofuran; chloroform;

DOI:10.1039/c0ob00643b

upstream raw materials:

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

(S)-tert-butyl 4-((R,Z)-1-(benzyloxy)-4-hydroxybut-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

(S)-tert-butyl 4-((R,Z)-4-acetoxy-1-(benzyloxy)but-2-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate

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

Downstream raw materials:

tert-butyl ((3S,4S,5R)-4-(benzyloxy)-5-((E)-tetradec-1-en-1-yl)tetrahydrofuran-3-yl)carbamate