(R)-3-(benzyloxymethyl)cyclopent-3-enyl acetate

Base Information

• Chemical Name: (R)-3-(benzyloxymethyl)cyclopent-3-enyl acetate
• CAS No.: 1403561-38-5
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.306
• Mol file: 1403561-38-5.mol

Synonyms:(R)-3-(benzyloxymethyl)cyclopent-3-enyl acetate

Chemical Property of (R)-3-(benzyloxymethyl)cyclopent-3-enyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(benzyloxymethyl)cyclopent-3-enyl acetate

There total 1 articles about (R)-3-(benzyloxymethyl)cyclopent-3-enyl acetate 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: 33.0%

(+/-)-3-[(benzyloxy)methyl]cyclopent-3-en-1-ol (153186-83-5) + vinyl acetate (108-05-4,9003-20-7) → (S)-3-(benzyloxymethyl)cyclopent-3-enol (1417654-97-7) + (R)-3-(benzyloxymethyl)cyclopent-3-enyl acetate (1403561-38-5) + (R)-3-(benzyloxymethyl)cyclopent-3-enol

Guidance literature:

With pancreatin from porcine pancreas; triethylamine; In acetone; at 20 ℃; for 23h; optical yield given as %ee; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1002/chem.201200733

Reference yield: 99.0%

(R)-3-(benzyloxymethyl)cyclopent-3-enyl acetate (1403561-38-5) → (R)-3-(benzyloxymethyl)cyclopent-3-enol

Guidance literature:

With methanol; sodium hydroxide; at 20 ℃; for 2h;

DOI:10.1002/chem.201200733

Reference yield:

(R)-3-(benzyloxymethyl)cyclopent-3-enyl acetate (1403561-38-5) → 5'-O-benzyl-2',3'-dideoxy-3',4'-didehydro-carba-L-cytidine (1403561-44-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: methanol; sodium hydroxide / 2 h / 20 °C

2.1: di-isopropyl azodicarboxylate; triphenylphosphine; benzoic acid / diethyl ether / 16 h / 0 - 20 °C

3.1: di-isopropyl azodicarboxylate; triphenylphosphine / acetonitrile / -40 - 20 °C / Inert atmosphere

4.1: methanol; sodium hydroxide / 20 °C

5.1: 1,2,4-Triazole; triethylamine; trichlorophosphate / acetonitrile / 48 h / 0 - 20 °C / Inert atmosphere

5.2: 168 h

With 1,2,4-Triazole; methanol; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; benzoic acid; sodium hydroxide; trichlorophosphate; In diethyl ether; acetonitrile; 2.1: Mitsunobu reaction / 3.1: Mitsunobu reaction;

DOI:10.1002/chem.201200733

upstream raw materials:

(+/-)-3-[(benzyloxy)methyl]cyclopent-3-en-1-ol

vinyl acetate

Downstream raw materials:

C₁₈H₂₂N₂O₅

C₁₈H₂₂N₂O₄

5'-O-benzyl-3'-deoxy-3',4'-didehydro-carba-D-thymidine

5'-O-benzyl-3'-deoxy-3',4'-didehydro-carba-L-thymidine