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

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Chemical Name:(2R,2'S,5'R,2''R,5''S)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one
CAS No.:862555-70-2
Molecular Formula:C₂₃H₃₂O₆
Molecular Weight:404.503
Hs Code.:

Synonyms:

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

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

There total 11 articles about (2R,2'S,5'R,2''R,5''S)-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:

: 862557-97-9
(4E,8E)-12-Benzyloxy-dodeca-4,8-dienal

: 862555-70-2
(2R,2'S,5'R,2''R,5''S)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one

Guidance literature:: Multi-step reaction with 8 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: oxone; K₂CO₃; Na₂B₄O₇*10H₂O / L-fructose-based (+)-Shi catalyst; nBu₄NHSO₄ / H₂O; various solvent(s); acetonitrile / 2.5 h / 0 °C

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

6.1: triethylamine

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

8.1: pyridine / 2 h / 140 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; borax; Oxone; n-butyllithium; diethyl (2R,3R)-tartrate; methanesulfonamide; camphor-10-sulfonic acid; potassium carbonate; triethylamine; diisopropylamine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); L-fructose-based (+)-Shi catalyst; tetra(n-butyl)ammonium hydrogensulfate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 2.1: Sharpless asymmetric epoxidation / 4.1: Shi asymmetric epoxidation / 7.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo050697c

Reference yield:

: 862557-57-1
(4E,8E)-12-Benzyloxy-dodeca-4,8-dien-1-ol

: 862555-70-2
(2R,2'S,5'R,2''R,5''S)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one

Guidance literature:: Multi-step reaction with 9 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: oxone; K₂CO₃; Na₂B₄O₇*10H₂O / L-fructose-based (+)-Shi catalyst; nBu₄NHSO₄ / H₂O; various solvent(s); acetonitrile / 2.5 h / 0 °C

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

7.1: triethylamine

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

9.1: pyridine / 2 h / 140 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; borax; Oxone; n-butyllithium; oxalyl dichloride; diethyl (2R,3R)-tartrate; methanesulfonamide; camphor-10-sulfonic acid; potassium carbonate; dimethyl sulfoxide; triethylamine; diisopropylamine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); L-fructose-based (+)-Shi catalyst; tetra(n-butyl)ammonium hydrogensulfate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1.1: Swern oxidation / 3.1: Sharpless asymmetric epoxidation / 5.1: Shi asymmetric epoxidation / 8.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo050697c

Reference yield:

: 862557-60-6
(6E,10E)-14-Benzyloxy-tetradeca-1,6,10-trien-3-ol

: 862555-70-2
(2R,2'S,5'R,2''R,5''S)-5''-((S)-4-Benzyloxy-1-hydroxy-butyl)-hexahydro-[2,2';5',2'']terfuran-5-one

Guidance literature:: Multi-step reaction with 7 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: oxone; K₂CO₃; Na₂B₄O₇*10H₂O / L-fructose-based (+)-Shi catalyst; nBu₄NHSO₄ / H₂O; various solvent(s); acetonitrile / 2.5 h / 0 °C

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

5.1: triethylamine

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

7.1: pyridine / 2 h / 140 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; borax; Oxone; n-butyllithium; diethyl (2R,3R)-tartrate; methanesulfonamide; camphor-10-sulfonic acid; potassium carbonate; triethylamine; diisopropylamine; potassium hexacyanoferrate(III); potassium dioxotetrahydroxoosmate(VI); L-fructose-based (+)-Shi catalyst; tetra(n-butyl)ammonium hydrogensulfate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1.1: Sharpless asymmetric epoxidation / 3.1: Shi asymmetric epoxidation / 6.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo050697c