((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate

Base Information

Chemical Name:((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate
CAS No.:80923-96-2
Molecular Formula:C₁₄H₁₄O₅
Molecular Weight:262.262
Hs Code.:

Synonyms:((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of ((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate

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Technology Process of ((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate

There total 16 articles about ((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate 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: 87.0%

: ((3aR,5S,6R,6aR)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

: 80923-96-2
((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate

Guidance literature:: ((3aR,5S,6R,6aR)-6-(2-ethoxy-2-oxoethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate; With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.0833333h;

With triethylsilane; In dichloromethane; at -78 - 23 ℃; for 6h;
DOI:10.1021/acs.joc.0c02396

Reference yield:

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 80923-96-2
((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 23 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C / Inert atmosphere

2.2: 1 h / 0 - 23 °C / Inert atmosphere

3.1: water; acetic acid / 60 h / 23 °C

4.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C

4.2: 6 h / -78 - 23 °C

With oxalyl dichloride; boron trifluoride diethyl etherate; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; water; acetic acid; mineral oil; 1.1: |Swern Oxidation / 1.2: |Swern Oxidation;
DOI:10.1021/acs.joc.0c02396

Reference yield:

: 59256-86-9
ethyl 2-((3aR,5S,6R,6aR)-5-((R)-1,2-dihydroxyethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)acetate

: 80923-96-2
((3aR,4S,6aR)-2-oxohexahydrofuro[3,4-b]furan-4-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium periodate / methanol / 2 h / 0 - 23 °C

2.1: sodium tetrahydroborate / methanol / 1 h / 0 °C

3.1: triethylamine / dichloromethane / 18 h / 0 - 23 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C

4.2: 6 h / -78 - 23 °C

With sodium tetrahydroborate; sodium periodate; boron trifluoride diethyl etherate; triethylamine; In methanol; dichloromethane;
DOI:10.1021/acs.joc.0c02396