Cyclopentanecarboxylic acid, 2-methyl-3-oxo-, methyl ester, (1S,2R)- (9CI)

Base Information

• Chemical Name: Cyclopentanecarboxylic acid, 2-methyl-3-oxo-, methyl ester, (1S,2R)- (9CI)
• CAS No.: 777918-06-6
• Molecular Formula: C8H12 O3
• Molecular Weight: 156.17908
• Mol file: 777918-06-6.mol

Synonyms:Cyclopentanecarboxylic acid, 2-methyl-3-oxo-, methyl ester, (1S,2R)- (9CI)

Chemical Property of Cyclopentanecarboxylic acid, 2-methyl-3-oxo-, methyl ester, (1S,2R)- (9CI)

Chemical Property:

• PSA: 43.37000
• LogP: 0.77460

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopentanecarboxylic acid, 2-methyl-3-oxo-, methyl ester, (1S,2R)- (9CI)

There total 11 articles about Cyclopentanecarboxylic acid, 2-methyl-3-oxo-, methyl ester, (1S,2R)- (9CI) 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:

diethyl 2-oxo-hept-6-enephosphonate (123444-56-4) → methyl (-)-trans-2-methylcyclopentan-3-one-1-carboxylate (777918-06-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH, 2.) TosN₃ / 1.) benzene, THF, 0 deg C, 1.5 h, 2.) benzene, THF, RT, 3 h

2: 58 percent / dirhodium(II) tetraacetate / CH₂Cl₂ / 2 h / Heating

3: 1.) O₃, 2.) Me₂S / 1.) MeOH, -70 deg C, 2.) MeOH, from -10 deg C to RT, 3 h

4: CrO₃, aq. H₂SO₄ / acetone / 0.5 h

5: diethyl ether / 0.5 h / Ambient temperature

6: H20, phosphate buffer, α-chymotrypsin

7: 1.) NaH / 1.) THF, RT, 1.5 h, 2.) THF, 40 deg C, 1 h

8: H₂ / 10percent Pd/C / methanol / 0.33 h / 760 Torr

9: diethyl ether / 0 °C

With chromium(VI) oxide; dirhodium tetraacetate; 4-toluenesulfonyl azide; phosphate buffer; dimethylsulfide; sulfuric acid; water; hydrogen; sodium hydride; ozone; α-chymotrypsin; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; acetone;

DOI:10.1055/s-1997-1193

Reference yield:

((1S,5S)-2-Oxo-5-vinyl-cyclopentyl)-phosphonic acid diethyl ester → methyl (-)-trans-2-methylcyclopentan-3-one-1-carboxylate (777918-06-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) O₃, 2.) Me₂S / 1.) MeOH, -70 deg C, 2.) MeOH, from -10 deg C to RT, 3 h

2: CrO₃, aq. H₂SO₄ / acetone / 0.5 h

3: diethyl ether / 0.5 h / Ambient temperature

4: H20, phosphate buffer, α-chymotrypsin

5: 1.) NaH / 1.) THF, RT, 1.5 h, 2.) THF, 40 deg C, 1 h

6: H₂ / 10percent Pd/C / methanol / 0.33 h / 760 Torr

7: diethyl ether / 0 °C

With chromium(VI) oxide; phosphate buffer; dimethylsulfide; sulfuric acid; water; hydrogen; sodium hydride; ozone; α-chymotrypsin; palladium on activated charcoal; In methanol; diethyl ether; acetone;

DOI:10.1055/s-1997-1193

Reference yield:

(3-Diazo-2-oxo-hept-6-enyl)-phosphonic acid diethyl ester → methyl (-)-trans-2-methylcyclopentan-3-one-1-carboxylate (777918-06-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 58 percent / dirhodium(II) tetraacetate / CH₂Cl₂ / 2 h / Heating

2: 1.) O₃, 2.) Me₂S / 1.) MeOH, -70 deg C, 2.) MeOH, from -10 deg C to RT, 3 h

3: CrO₃, aq. H₂SO₄ / acetone / 0.5 h

4: diethyl ether / 0.5 h / Ambient temperature

5: H20, phosphate buffer, α-chymotrypsin

6: 1.) NaH / 1.) THF, RT, 1.5 h, 2.) THF, 40 deg C, 1 h

7: H₂ / 10percent Pd/C / methanol / 0.33 h / 760 Torr

8: diethyl ether / 0 °C

With chromium(VI) oxide; dirhodium tetraacetate; phosphate buffer; dimethylsulfide; sulfuric acid; water; hydrogen; sodium hydride; ozone; α-chymotrypsin; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; acetone;

DOI:10.1055/s-1997-1193

upstream raw materials:

diazomethane

(S,R)-(-)-dihydrosarkomycin

trans-2-methyl-3-oxocyclopentane carboxylic acid

sarcomycin

Downstream raw materials:

methyl (+)-trans-3-methylcyclopentene-4-carboxylate

3ξ-Hydroxy-2r-methyl-cyclopentan-1t-carbonsaeure-methylester

Refernces

• 1、 Miko?ajczyk, Marian,Zurawiński, Remigiusz,Kie?basin?ski, Piotr,Wieczorek, Micha? W.,B?aszczyk, Jaros?aw,Majzner, Wies?aw R.. "Total synthesis of racemic and optically active sarkomycin". . p. 356 - 365. Retrieved 2007/10/03.