2-((1S,4S,5R)-5-Benzyloxymethyl-4-methyl-cyclopent-2-enyl)-propionic acid

Base Information

• Chemical Name: 2-((1S,4S,5R)-5-Benzyloxymethyl-4-methyl-cyclopent-2-enyl)-propionic acid
• CAS No.: 77256-88-3
• Molecular Formula: C₁₇H₂₂O₃
• Molecular Weight: 274.36

Synonyms:2-((1S,4S,5R)-5-Benzyloxymethyl-4-methyl-cyclopent-2-enyl)-propionic acid

Chemical Property of 2-((1S,4S,5R)-5-Benzyloxymethyl-4-methyl-cyclopent-2-enyl)-propionic acid

Chemical Property:

Purity/Quality:

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Technology Process of 2-((1S,4S,5R)-5-Benzyloxymethyl-4-methyl-cyclopent-2-enyl)-propionic acid

There total 7 articles about 2-((1S,4S,5R)-5-Benzyloxymethyl-4-methyl-cyclopent-2-enyl)-propionic acid 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: 84.0%

(+/-)(3R*,3aR*,4S*,6aR*)-3,3a,4,6a-tetrahydro-3-methyl-4-<(benzyloxy)methyl>-2H-cyclopentafuran-2-one (77256-85-0) → 2-((1S,4S,5R)-5-Benzyloxymethyl-4-methyl-cyclopent-2-enyl)-propionic acid (77256-88-3)

Guidance literature:

In diethyl ether; at -20 ℃; for 1.25h;

DOI:10.1021/jo00325a035

Reference yield:

benzyl bromide (100-39-0) → 2-((1S,4S,5R)-5-Benzyloxymethyl-4-methyl-cyclopent-2-enyl)-propionic acid (77256-88-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) benzene, dimethyl sulfoxide, 60 deg C, 4 h, 2.) 8 h

2: 97 percent / 10percent HCl / tetrahydrofuran / 18 h / Ambient temperature

3: NaOH, H₂O₂ / 1.) THF, CH₃OH, H₂O, 0 deg C, 1 h, 2.) room temp., 24 h

4: borontrifluoride etherate / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temp., 30 min

5: 1.) lithium diisopropylamide

6: 84 percent / diethyl ether / 1.25 h / -20 °C

With hydrogenchloride; sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo00325a035

Reference yield:

(1R*,4S*,7S*)-7-<(benzyloxy)methyl>bicyclo<2.2.1>hept-5-en-2-one (77256-87-2) → 2-((1S,4S,5R)-5-Benzyloxymethyl-4-methyl-cyclopent-2-enyl)-propionic acid (77256-88-3)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOH, H₂O₂ / 1.) THF, CH₃OH, H₂O, 0 deg C, 1 h, 2.) room temp., 24 h

2: borontrifluoride etherate / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temp., 30 min

3: 1.) lithium diisopropylamide

4: 84 percent / diethyl ether / 1.25 h / -20 °C

With sodium hydroxide; boron trifluoride diethyl etherate; dihydrogen peroxide; lithium diisopropyl amide; In diethyl ether; dichloromethane;

DOI:10.1021/jo00325a035

upstream raw materials:

(+/-)(3R^*,3aR^*,4S^*,6aR^*)-3,3a,4,6a-tetrahydro-3-methyl-4-<(benzyloxy)methyl>-2H-cyclopentafuran-2-one

benzyl bromide

(1R^*,4S^*,7S^*)-7-<(benzyloxy)methyl>bicyclo<2.2.1>hept-5-en-2-one

(+/-)(3aR^*,4R^*,6aS^*)-3,3a,4,6a-tetrahydro-4-<(benzyloxy)-methyl>-2H-cyclopentafuran-1-one

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