(+)-2-oxabicyclo<3.3.0>octan-3-one

Base Information

• Chemical Name: (+)-2-oxabicyclo<3.3.0>octan-3-one
• CAS No.: 100100-47-8
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.155
• Mol file: 100100-47-8.mol

Synonyms:

Chemical Property of (+)-2-oxabicyclo<3.3.0>octan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-2-oxabicyclo<3.3.0>octan-3-one

There total 1 articles about (+)-2-oxabicyclo<3.3.0>octan-3-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:

(E)-7-Oxo-hept-2-enoic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester (634189-19-8) → (3aS,6aS)-hexahydrocyclopenta[b]furan-2-one (43119-29-5) + (+)-2-oxabicyclo<3.3.0>octan-3-one (100100-47-8) + ((1S,2R)-2-Hydroxy-cyclopentyl)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester + ((1R,2S)-2-Hydroxy-cyclopentyl)-acetic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester (634189-21-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃;

DOI:10.1016/j.tetasy.2003.07.006

Reference yield:

(+)-2-oxabicyclo<3.3.0>octan-3-one (100100-47-8) → [(1R,5S,7R)-1-((R)-2-Benzyloxy-1-methyl-ethyl)-6-(2,2,2-trifluoro-acetyl)-6-aza-spiro[4.5]dec-7-yl]-acetaldehyde (857685-74-6)

Guidance literature:

Multi-step reaction with 17 steps

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / 6 h / -78 °C

2.1: LiAlH₄ / tetrahydrofuran / 4 h / Heating

3.1: sodium hydride / tetrahydrofuran / 10 h / 20 °C

4.1: pyridinium chlorochromate; Celite / CH₂Cl₂ / 4 h / 20 °C

5.1: hydroxylamine hydrochloride; potassium carbonate / methanol / 4 h / 20 °C

6.1: m-CPBA; Na₂HPO₄; urea / acetonitrile / 80 °C

7.1: Triton B / methanol; tetrahydrofuran; 2-methyl-propan-2-ol / 48 h / 20 °C

8.1: LiBH₄ / tetrahydrofuran / 24 h / 20 °C

9.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

10.1: sodium iodide; sodium hydrogen carbonate / acetone / 24 h / 20 °C

11.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

11.2: tetrahydrofuran; pentane / 3 h / -78 °C

12.1: iodine; sodium hydrogen carbonate / acetone; H₂O / 1 h / 0 °C

13.1: hydrogen; triethylamine / Raney nickel / cyclohexane / 4 h / 25 °C / 760.05 Torr

14.1: NaBH₄ / CH₂Cl₂; methanol / 0 - 20 °C

15.1: i-Pr₂NEt / 1,2-dichloro-ethane / 1 h / 0 °C

16.1: HF*pyridine complex / tetrahydrofuran / 20 °C

17.1: DMP / CH₂Cl₂ / 5 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; lithium borohydride; phthalic acid dimethyl ester; Celite; hydroxylamine hydrochloride; hydrogen; iodine; tert.-butyl lithium; N-benzyl-trimethylammonium hydroxide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; urea; pyridinium chlorochromate; sodium iodide; lithium diisopropyl amide; nickel; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; water; 1,2-dichloro-ethane; acetone; acetonitrile; tert-butyl alcohol; pentane; 7.1: Michael addition;

DOI:10.1016/j.tet.2007.03.031

Reference yield:

(+)-2-oxabicyclo<3.3.0>octan-3-one (100100-47-8) → 1-(R)-(2'-benzyloxy-1'-(R)-methyl-ethyl)-7-(R)-[2''-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6-aza-5-(S)-spiro[4.5]decane (857685-70-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / 6 h / -78 °C

2.1: LiAlH₄ / tetrahydrofuran / 4 h / Heating

3.1: sodium hydride / tetrahydrofuran / 10 h / 20 °C

4.1: pyridinium chlorochromate; Celite / CH₂Cl₂ / 4 h / 20 °C

5.1: hydroxylamine hydrochloride; potassium carbonate / methanol / 4 h / 20 °C

6.1: m-CPBA; Na₂HPO₄; urea / acetonitrile / 80 °C

7.1: Triton B / methanol; tetrahydrofuran; 2-methyl-propan-2-ol / 48 h / 20 °C

8.1: LiBH₄ / tetrahydrofuran / 24 h / 20 °C

9.1: triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

10.1: sodium iodide; sodium hydrogen carbonate / acetone / 24 h / 20 °C

11.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 0.5 h / -78 °C

11.2: tetrahydrofuran; pentane / 3 h / -78 °C

12.1: iodine; sodium hydrogen carbonate / acetone; H₂O / 1 h / 0 °C

13.1: hydrogen; triethylamine / Raney nickel / cyclohexane / 4 h / 25 °C / 760.05 Torr

14.1: NaBH₄ / CH₂Cl₂; methanol / 0 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; lithium borohydride; Celite; hydroxylamine hydrochloride; hydrogen; iodine; tert.-butyl lithium; N-benzyl-trimethylammonium hydroxide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; urea; pyridinium chlorochromate; sodium iodide; lithium diisopropyl amide; nickel; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; water; acetone; acetonitrile; tert-butyl alcohol; pentane; 7.1: Michael addition;

DOI:10.1016/j.tet.2007.03.031

upstream raw materials:

(E)-7-Oxo-hept-2-enoic acid (3R,3aR,6S,6aR)-6-benzyloxy-hexahydro-furo[3,2-b]furan-3-yl ester

Downstream raw materials:

(2R)-2-((1R)-2-benzyloxy-1-methylethyl)-cyclopentanone

(2R)-2-((1R)-2-benzyloxy-1-methylethyl)-cyclopentanone oxime

(1R)-1-((1R)-2-benzyloxy-1-methylethyl)-2-nitrocyclopentane

1-(R)-(2'-benzyloxy-1'-(R)-methyl-ethyl)-2-(S)-(3''-iodo-propyl)-2-(S)-nitro-cyclopentane