(+)-(3S,5S)-3-allyl-3-ethyl-5-trityloxymethyltetrahydrofuran-2-one

Base Information

• Chemical Name: (+)-(3S,5S)-3-allyl-3-ethyl-5-trityloxymethyltetrahydrofuran-2-one
• CAS No.: 75652-71-0
• Molecular Formula: C₂₉H₃₀O₃
• Molecular Weight: 426.555
• Mol file: 75652-71-0.mol

Synonyms:(+)-(3S,5S)-3-allyl-3-ethyl-5-trityloxymethyltetrahydrofuran-2-one

Chemical Property of (+)-(3S,5S)-3-allyl-3-ethyl-5-trityloxymethyltetrahydrofuran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3S,5S)-3-allyl-3-ethyl-5-trityloxymethyltetrahydrofuran-2-one

There total 4 articles about (+)-(3S,5S)-3-allyl-3-ethyl-5-trityloxymethyltetrahydrofuran-2-one 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: 92.5%

ethyl bromide (74-96-4) + (+)-(3R,5S)-3-allyl-5-trityloxymethyltetrahydrofuran-2-one (75652-70-9) → (+)-(3S,5S)-3-allyl-3-ethyl-5-trityloxymethyltetrahydrofuran-2-one (75652-71-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃; for 20h;

DOI:10.1039/c39800000616

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (+)-(3S,5S)-3-allyl-3-ethyl-5-trityloxymethyltetrahydrofuran-2-one (75652-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / pyridine / 20 h / Ambient temperature

2: 96 percent / LiN(iPr)2 / tetrahydrofuran / 4 h / -78 - -30 °C

3: 92.5 percent / LiN(iPr)2 / tetrahydrofuran / 20 h / -78 - 20 °C

With lithium diisopropyl amide; In tetrahydrofuran; pyridine;

DOI:10.1039/c39800000616

Reference yield:

(5S)-5-[(trityloxy)methyl]tetrahydro-2-furanone (73968-62-4) → (+)-(3S,5S)-3-allyl-3-ethyl-5-trityloxymethyltetrahydrofuran-2-one (75652-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / LiN(iPr)2 / tetrahydrofuran / 4 h / -78 - -30 °C

2: 92.5 percent / LiN(iPr)2 / tetrahydrofuran / 20 h / -78 - 20 °C

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1039/c39800000616

upstream raw materials:

ethyl bromide

(+)-(3R,5S)-3-allyl-5-trityloxymethyltetrahydrofuran-2-one

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

L-glutamic acid

Downstream raw materials:

(3S,5S)-3-Ethyl-3-(3-hydroxy-propyl)-5-trityloxymethyl-dihydro-furan-2-one