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

Base Information

Chemical Name:(2R,2'S,5'S)-5'-((E)-(R)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one
CAS No.:862557-25-3
Molecular Formula:C₂₃H₃₂O₅
Molecular Weight:388.504
Hs Code.:

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

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

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

There total 9 articles about (2R,2'S,5'S)-5'-((E)-(R)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-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: 76.0%

: 862557-04-8
(R)-5-((4Z,8E)-(S)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one

: 862557-25-3
(2R,2'S,5'S)-5'-((E)-(R)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one

Guidance literature:: With 2,6-dimethylpyridine; rhenium(VII) oxide; trifluoroacetic anhydride; In dichloromethane; at 0 - 20 ℃; for 6h;
DOI:10.1021/jo050697c

Reference yield:

: 862558-02-9
((E)-8-Iodo-oct-4-enyloxymethyl)-benzene

: 862557-25-3
(2R,2'S,5'S)-5'-((E)-(R)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one

Guidance literature:: Multi-step reaction with 7 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

With 2,6-dimethylpyridine; sodium hydroxide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydrogencarbonate; toluene-4-sulfonic acid; rhenium(VII) oxide; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2.2: Wittig reaction / 4.1: Mitsunobu reaction;
DOI:10.1021/jo050697c

Reference yield:

: 862556-98-7
(R)-5-((4Z,8E)-(R)-12-Benzyloxy-1-hydroxy-dodeca-4,8-dienyl)-dihydro-furan-2-one

: 862557-25-3
(2R,2'S,5'S)-5'-((E)-(R)-8-Benzyloxy-1-hydroxy-oct-4-enyl)-tetrahydro-[2,2']bifuranyl-5-one

Guidance literature:: Multi-step reaction with 4 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

With 2,6-dimethylpyridine; sodium hydroxide; di-isopropyl azodicarboxylate; toluene-4-sulfonic acid; rhenium(VII) oxide; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; 1: Mitsunobu reaction;
DOI:10.1021/jo050697c