(2R,2'S,5'S,2''R,5''R)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one

Base Information

• Chemical Name: (2R,2'S,5'S,2''R,5''R)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one
• CAS No.: 862556-20-5
• Molecular Formula: C₂₃H₃₂O₆
• Molecular Weight: 404.503
• Mol file: 862556-20-5.mol

Synonyms:(2R,2'S,5'S,2''R,5''R)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one

Chemical Property of (2R,2'S,5'S,2''R,5''R)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,2'S,5'S,2''R,5''R)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one

There total 11 articles about (2R,2'S,5'S,2''R,5''R)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-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:

(2R,2'S,5'S)-5'-{(R)-3-[(2S,3S)-3-(3-Benzyloxy-propyl)-oxiranyl]-1-hydroxy-propyl}-tetrahydro-[2,2']bifuranyl-5-one → (2R,2'S,5'S,2''R,5''R)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one (862556-20-5)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; dichloromethane; at 0 ℃;

DOI:10.1021/jo050697c

Reference yield:

((E)-8-Iodo-oct-4-enyloxymethyl)-benzene (862558-02-9) → (2R,2'S,5'S,2''R,5''R)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one (862556-20-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 80 percent / NaHCO₃ / acetonitrile / 8 h / Heating

2.1: NaHMDS / tetrahydrofuran / 2 h / -78 °C

2.2: HMPA / tetrahydrofuran / 3.5 h / -78 - 0 °C

3.1: TBAF / tetrahydrofuran / 4 h

4.1: diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 12 h / 20 °C

5.1: aqueous NaOH / methanol / 2 h / 60 °C

6.1: PTSA*H₂O / CH₂Cl₂ / 1 h / 20 °C

7.1: 76 percent / TFAA; Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 20 °C

8.1: oxone; K₂CO₃; Na₂B₄O₇*10H₂O / L-fructose-based (+)-Shi catalyst; nBu₄NHSO₄ / H₂O; various solvent(s); acetonitrile / 2.5 h / 0 °C

9.1: camphorsulfonic acid / CH₂Cl₂; methanol / 0 °C

With 2,6-dimethylpyridine; borax; Oxone; sodium hydroxide; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; triphenylphosphine; trifluoroacetic anhydride; L-fructose-based (+)-Shi catalyst; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 2.2: Wittig reaction / 4.1: Mitsunobu reaction / 8.1: Shi asymmetric epoxidation;

DOI:10.1021/jo050697c

Reference yield:

(R)-5-((4Z,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one (862556-98-7) → (2R,2'S,5'S,2''R,5''R)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one (862556-20-5)

Guidance literature:

Multi-step reaction with 6 steps

1: diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 12 h / 20 °C

2: aqueous NaOH / methanol / 2 h / 60 °C

3: PTSA*H₂O / CH₂Cl₂ / 1 h / 20 °C

4: 76 percent / TFAA; Re₂O₇; 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 20 °C

5: oxone; K₂CO₃; Na₂B₄O₇*10H₂O / L-fructose-based (+)-Shi catalyst; nBu₄NHSO₄ / H₂O; various solvent(s); acetonitrile / 2.5 h / 0 °C

6: camphorsulfonic acid / CH₂Cl₂; methanol / 0 °C

With 2,6-dimethylpyridine; borax; Oxone; sodium hydroxide; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; potassium carbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; triphenylphosphine; trifluoroacetic anhydride; L-fructose-based (+)-Shi catalyst; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1: Mitsunobu reaction / 5: Shi asymmetric epoxidation;

DOI:10.1021/jo050697c

upstream raw materials:

((E)-8-Iodo-oct-4-enyloxymethyl)-benzene

(R)-5-((4Z,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one

(R)-5-((4Z,8E)-(S)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one

(2R,2'S,5'S)-5'-((E)-(R)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one