(1'R,3aR,5R,7aR)-5-(1',2'-dibenzyloxy-ethyl)-hexahydro-furo[3,2-b]pyran-2-one

Base Information

Chemical Name:(1'R,3aR,5R,7aR)-5-(1',2'-dibenzyloxy-ethyl)-hexahydro-furo[3,2-b]pyran-2-one
CAS No.:860267-65-8
Molecular Formula:C₂₃H₂₆O₅
Molecular Weight:382.456
Hs Code.:

Synonyms:(1'R,3aR,5R,7aR)-5-(1',2'-dibenzyloxy-ethyl)-hexahydro-furo[3,2-b]pyran-2-one

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Chemical Property of (1'R,3aR,5R,7aR)-5-(1',2'-dibenzyloxy-ethyl)-hexahydro-furo[3,2-b]pyran-2-one

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Technology Process of (1'R,3aR,5R,7aR)-5-(1',2'-dibenzyloxy-ethyl)-hexahydro-furo[3,2-b]pyran-2-one

There total 10 articles about (1'R,3aR,5R,7aR)-5-(1',2'-dibenzyloxy-ethyl)-hexahydro-furo[3,2-b]pyran-2-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:

: 860267-59-0
(4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane

: 860267-65-8
(1'R,3aR,5R,7aR)-5-(1',2'-dibenzyloxy-ethyl)-hexahydro-furo[3,2-b]pyran-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / NaIO₄ / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

2: 74 percent / d-camphorsulfonic acid / methanol / 18 h / 0 °C

3: 96 percent / n-tetrabutylammonium iodide; sodium hydride / dimethylformamide / 2 h / 0 - 20 °C

4: 98 percent / zinc triflate / 1,2-dichloro-ethane / 6 h / 50 °C

5: 97 percent / N-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

6: 85 percent / iodomethane; NaHCO₃ / acetonitrile; H₂O / 28 h / 0 - 20 °C

7: 86 percent / samarium(II) iodide; methanol / tetrahydrofuran / 1 h / 0 °C

8: 1.31 g / aq. NaOH / ethanol / 2.5 h / 20 °C

9: 1.15 g / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 2 h

With 4-methyl-morpholine; methanol; sodium hydroxide; sodium periodate; samarium diiodide; (1S)-10-camphorsulfonic acid; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; methyl iodide; osmium(VIII) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 1: Lemieux-Johnson oxidation / 5: oxy-Michael addition / 9: Mitsunobu reaction;
DOI:10.1021/ol0508126

Reference yield:

: 133842-56-5
Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

: 860267-65-8
(1'R,3aR,5R,7aR)-5-(1',2'-dibenzyloxy-ethyl)-hexahydro-furo[3,2-b]pyran-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: CuBr / diethyl ether / 0.25 h / 0 °C

1.2: 11.2 g / diethyl ether / 2.5 h / 0 °C

2.1: 90 percent / NaIO₄ / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

3.1: 74 percent / d-camphorsulfonic acid / methanol / 18 h / 0 °C

4.1: 96 percent / n-tetrabutylammonium iodide; sodium hydride / dimethylformamide / 2 h / 0 - 20 °C

5.1: 98 percent / zinc triflate / 1,2-dichloro-ethane / 6 h / 50 °C

6.1: 97 percent / N-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

7.1: 85 percent / iodomethane; NaHCO₃ / acetonitrile; H₂O / 28 h / 0 - 20 °C

8.1: 86 percent / samarium(II) iodide; methanol / tetrahydrofuran / 1 h / 0 °C

9.1: 1.31 g / aq. NaOH / ethanol / 2.5 h / 20 °C

10.1: 1.15 g / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 2 h

With 4-methyl-morpholine; methanol; sodium hydroxide; sodium periodate; samarium diiodide; (1S)-10-camphorsulfonic acid; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; sodium hydrogencarbonate; triphenylphosphine; copper(I) bromide; diethylazodicarboxylate; methyl iodide; osmium(VIII) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 2.1: Lemieux-Johnson oxidation / 6.1: oxy-Michael addition / 10.1: Mitsunobu reaction;
DOI:10.1021/ol0508126