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

Base Information

• Chemical Name: (2R,2'R,5'S,2''S,5''R)-5''-((R)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one
• CAS No.: 862555-67-7
• Molecular Formula: C₂₃H₃₂O₆
• Molecular Weight: 404.503
• Mol file: 862555-67-7.mol

Synonyms:

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

There total 14 articles about (2R,2'R,5'S,2''S,5''R)-5''-((R)-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:

(4E,8E)-12-Benzyloxy-dodeca-4,8-dienal (862557-97-9) → (2R,2'R,5'S,2''S,5''R)-5''-((R)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one (862555-67-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 60 percent / diethyl ether; tetrahydrofuran / 1 h / -78 °C

2.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; tert-BuOOH / CH₂Cl₂; hexane / 48 h / -20 °C

3.1: n-BuLi; iPr₂NH / tetrahydrofuran; hexane / 0.42 h

3.2: tetrahydrofuran; hexane / 3 h / Heating

3.3: PTSA*H₂O / benzene / 1 h / Heating

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

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

9.1: triethylamine

10.1: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / K₂OsO₂(OH)4; (DHQD)PHAL / H₂O; 2-methyl-propan-2-ol / 0 °C

11.1: pyridine / 2 h / 140 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; borax; Oxone; sodium hydroxide; n-butyllithium; diethyl (2R,3R)-tartrate; methanesulfonamide; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; potassium carbonate; toluene-4-sulfonic acid; triethylamine; diisopropylamine; triphenylphosphine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); D-fructose-based (-)-Shi catalyst; tetra(n-butyl)ammonium hydrogensulfate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 2.1: Sharpless asymmetric epoxidation / 4.1: Mitsunobu reaction / 7.1: Shi asymmetric epoxidation / 10.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo050697c

Reference yield:

(4E,8E)-12-Benzyloxy-dodeca-4,8-dien-1-ol (862557-57-1) → (2R,2'R,5'S,2''S,5''R)-5''-((R)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one (862555-67-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 91 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2.1: 60 percent / diethyl ether; tetrahydrofuran / 1 h / -78 °C

3.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; tert-BuOOH / CH₂Cl₂; hexane / 48 h / -20 °C

4.1: n-BuLi; iPr₂NH / tetrahydrofuran; hexane / 0.42 h

4.2: tetrahydrofuran; hexane / 3 h / Heating

4.3: PTSA*H₂O / benzene / 1 h / Heating

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

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

7.1: PTSA*H₂O / CH₂Cl₂ / 1 h / 20 °C

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

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

10.1: triethylamine

11.1: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / K₂OsO₂(OH)4; (DHQD)PHAL / H₂O; 2-methyl-propan-2-ol / 0 °C

12.1: pyridine / 2 h / 140 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; borax; Oxone; sodium hydroxide; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; methanesulfonamide; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); D-fructose-based (-)-Shi catalyst; tetra(n-butyl)ammonium hydrogensulfate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1.1: Swern oxidation / 3.1: Sharpless asymmetric epoxidation / 5.1: Mitsunobu reaction / 8.1: Shi asymmetric epoxidation / 11.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo050697c

Reference yield:

(6E,10E)-14-Benzyloxy-tetradeca-1,6,10-trien-3-ol (862557-60-6) → (2R,2'R,5'S,2''S,5''R)-5''-((R)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one (862555-67-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; tert-BuOOH / CH₂Cl₂; hexane / 48 h / -20 °C

2.1: n-BuLi; iPr₂NH / tetrahydrofuran; hexane / 0.42 h

2.2: tetrahydrofuran; hexane / 3 h / Heating

2.3: PTSA*H₂O / benzene / 1 h / Heating

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

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

5.1: PTSA*H₂O / CH₂Cl₂ / 1 h / 20 °C

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

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

8.1: triethylamine

9.1: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / K₂OsO₂(OH)4; (DHQD)PHAL / H₂O; 2-methyl-propan-2-ol / 0 °C

10.1: pyridine / 2 h / 140 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; borax; Oxone; sodium hydroxide; n-butyllithium; diethyl (2R,3R)-tartrate; methanesulfonamide; di-isopropyl azodicarboxylate; camphor-10-sulfonic acid; potassium carbonate; toluene-4-sulfonic acid; triethylamine; diisopropylamine; triphenylphosphine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); D-fructose-based (-)-Shi catalyst; tetra(n-butyl)ammonium hydrogensulfate; (9S,9"S)-9,9"-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane]; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1.1: Sharpless asymmetric epoxidation / 3.1: Mitsunobu reaction / 6.1: Shi asymmetric epoxidation / 9.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo050697c

upstream raw materials:

(4E,8E)-12-Benzyloxy-dodeca-4,8-dienal

(4E,8E)-12-Benzyloxy-dodeca-4,8-dien-1-ol

(6E,10E)-14-Benzyloxy-tetradeca-1,6,10-trien-3-ol

(4E,8E)-(S)-12-Benzyloxy-1-(R)-oxiranyl-dodeca-4,8-dien-1-ol