(4S^*,5R^*)-5-(3,5-Dinitrophenylcarbonyloxy)-4-methoxy-5-methoxymethyl-2-cyclopentenone

Base Information

• Chemical Name: (4S^*,5R^*)-5-(3,5-Dinitrophenylcarbonyloxy)-4-methoxy-5-methoxymethyl-2-cyclopentenone
• CAS No.: 129076-61-5
• Molecular Formula: C₁₅H₁₄N₂O₉
• Molecular Weight: 366.284

Synonyms:(4S^*,5R^*)-5-(3,5-Dinitrophenylcarbonyloxy)-4-methoxy-5-methoxymethyl-2-cyclopentenone

Chemical Property of (4S^*,5R^*)-5-(3,5-Dinitrophenylcarbonyloxy)-4-methoxy-5-methoxymethyl-2-cyclopentenone

Chemical Property:

Purity/Quality:

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Technology Process of (4S^*,5R^*)-5-(3,5-Dinitrophenylcarbonyloxy)-4-methoxy-5-methoxymethyl-2-cyclopentenone

There total 2 articles about (4S^*,5R^*)-5-(3,5-Dinitrophenylcarbonyloxy)-4-methoxy-5-methoxymethyl-2-cyclopentenone 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: 70.0%

(4S*,5R*)-5-Hydroxy-4-methoxy-5-methoxymethyl-2-cyclopentenone (129076-60-4) + 3,5-dinitrobenoyl chloride (99-33-2) → (4S*,5R*)-5-(3,5-Dinitrophenylcarbonyloxy)-4-methoxy-5-methoxymethyl-2-cyclopentenone (129076-61-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; 1.) 0 deg C, 20 min, 2.) 2 h;

DOI:10.1016/S0040-4020(01)82039-1

Reference yield:

4,5-epoxy-5-methoxymethyl-2-cyclopentenone (112698-65-4,129076-44-4,130195-91-4) → (4S*,5R*)-5-(3,5-Dinitrophenylcarbonyloxy)-4-methoxy-5-methoxymethyl-2-cyclopentenone (129076-61-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / 5 N aq. H₂SO₄ / Ambient temperature

2: 70 percent / DMAP, Et₃N / CH₂Cl₂ / 1.) 0 deg C, 20 min, 2.) 2 h

With dmap; triethylamine; sulfuric acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)82039-1

upstream raw materials:

(4S^*,5R^*)-5-Hydroxy-4-methoxy-5-methoxymethyl-2-cyclopentenone

3,5-dinitrobenoyl chloride

4,5-epoxy-5-methoxymethyl-2-cyclopentenone

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