(3s,3Ar,6ar)-3-hydroxy-3,3a,4,6a-tetrahydro-2h-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3s,3Ar,6ar)-3-hydroxy-3,3a,4,6a-tetrahydro-2h-cyclopenta[b]furan-2-one
• CAS No.: 151765-22-9
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.139
• DSSTox Substance ID: DTXSID201151181
• Nikkaji Number: J518.952G
• Mol file: 151765-22-9.mol

Synonyms:(3s,3ar,6ar)-3-hydroxy-3,3a,4,6a-tetrahydro-2h-cyclopenta[b]furan-2-one;151765-22-9;(3S,3aR,6aR)-3-hydroxy-2H,3H,3aH,4H,6aH-cyclopenta[b]furan-2-one;DTXSID201151181;(3S,3aR,6aR)-3,3a,4,6a-Tetrahydro-3-hydroxy-2H-cyclopenta[b]furan-2-one

Chemical Property of (3s,3Ar,6ar)-3-hydroxy-3,3a,4,6a-tetrahydro-2h-cyclopenta[b]furan-2-one

Chemical Property:

• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 140.047344113
• Heavy Atom Count: 10
• Complexity: 197

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C=CC2C1C(C(=O)O2)O
• Isomeric SMILES: C1C=C[C@@H]2[C@H]1[C@@H](C(=O)O2)O

Technology Process of (3s,3Ar,6ar)-3-hydroxy-3,3a,4,6a-tetrahydro-2h-cyclopenta[b]furan-2-one

There total 2 articles about (3s,3Ar,6ar)-3-hydroxy-3,3a,4,6a-tetrahydro-2h-cyclopenta[b]furan-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: 41.0%

2,2-diphenylacetic acid (117-34-0) + 3-hydroxy-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one (139367-24-1,139491-15-9,141554-44-1,148555-09-3,148555-10-6) → (3R,3aR,6aS)-3,3a,4,6a-tetrahydro-2-oxo-2H-cyclopenta[b]furan-3-yl 2,2-diphenylacetate (1426302-87-5) + (3S,3aS,6aR)-3,3a,4,6a-tetrahydro-2-oxo-2H-cyclopenta[b]furan-3-yl 2,2-diphenylacetate + (3S,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (151765-22-9)

Guidance literature:

With (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine; In diethyl ether; at 20 ℃; for 12h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol303453j

Reference yield:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + Glyoxilic acid (298-12-4) → (3R,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (139367-24-1,139491-15-9,141554-44-1,148555-09-3,148555-10-6) + (3S,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (151765-22-9)

Guidance literature:

In water; at 0 - 20 ℃; for 96h; Overall yield = 65 percent; Overall yield = 183 g; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.0c00022

Reference yield:

(3S,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (151765-22-9) → abacavir (136470-78-5,128131-83-9,136470-79-6)

Guidance literature:

Multi-step reaction with 6 steps

1: LiAlH₄ / tetrahydrofuran / Heating

2: NaIO₄ / diethyl ether; H₂O

3: NaBH₄ / ethanol

4: 76 percent / Et₃N / CH₂Cl₂

5: 53 percent / Pd(PPh₃)4 / dimethylsulfoxide; tetrahydrofuran / 8 h / 60 °C

6: 72 percent / ethanol / Heating

With sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1039/a708261d

upstream raw materials:

2,2-diphenylacetic acid

3-hydroxy-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one

cyclopenta-1,3-diene

Glyoxilic acid

Downstream raw materials:

(1S,4S,5R)-4-benzyloxycarbonylamino-2-oxabicyclo[3.3.0]oct-7-ene-3-one

(1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol

abacavir

(S)-Benzyloxycarbonylamino-[(1S,4R)-4-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-cyclopent-2-enyl]-acetic acid