(3aR,5R,6R,6aR)-5-((S)-Benzyloxy-phenyl-methyl)-6-hydroxy-tetrahydro-furo[3,2-b]furan-2-one

Base Information

Chemical Name:(3aR,5R,6R,6aR)-5-((S)-Benzyloxy-phenyl-methyl)-6-hydroxy-tetrahydro-furo[3,2-b]furan-2-one
CAS No.:250598-94-8
Molecular Formula:C₂₀H₂₀O₅
Molecular Weight:340.376
Hs Code.:

Synonyms:(3aR,5R,6R,6aR)-5-((S)-Benzyloxy-phenyl-methyl)-6-hydroxy-tetrahydro-furo[3,2-b]furan-2-one

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Chemical Property of (3aR,5R,6R,6aR)-5-((S)-Benzyloxy-phenyl-methyl)-6-hydroxy-tetrahydro-furo[3,2-b]furan-2-one

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Technology Process of (3aR,5R,6R,6aR)-5-((S)-Benzyloxy-phenyl-methyl)-6-hydroxy-tetrahydro-furo[3,2-b]furan-2-one

There total 10 articles about (3aR,5R,6R,6aR)-5-((S)-Benzyloxy-phenyl-methyl)-6-hydroxy-tetrahydro-furo[3,2-b]furan-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: 78.0%

: (7S)-3,6-anhydro-7-O-benzyl-2-deoxy-7-C-phenyl-D-allo-1,4-heptanolactol

: 250598-94-8
(3aR,5R,6R,6aR)-5-((S)-Benzyloxy-phenyl-methyl)-6-hydroxy-tetrahydro-furo[3,2-b]furan-2-one

Guidance literature:: With dipyridinium dichromate; In dichloromethane; for 1.5h; Heating;
DOI:10.1016/S0968-0896(99)00164-9

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 250598-94-8
(3aR,5R,6R,6aR)-5-((S)-Benzyloxy-phenyl-methyl)-6-hydroxy-tetrahydro-furo[3,2-b]furan-2-one

Guidance literature:: Multi-step reaction with 12 steps

1: NaH / dimethylsulfoxide / 1 h / 0 - 20 °C

2: 26 percent / NaH / dimethylformamide / 0.5 h / 0 °C

3: 95 percent / H₂ / 10 percent Pd-BaSO₄ / methanol / 4 h

4: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

5: 58 percent / tetrahydrofuran / 4 h / 0 °C

6: 90 percent / NaH / dimethylformamide / 0.5 h / 20 °C

7: 85 percent / AcOH / H₂O / 8 h / 20 °C

8: 85 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

9: 82 percent / NaI / butan-2-one / 12 h / Heating

10: 82 percent / 5 percent aq. H₂SO₄ / dioxane / 1 h / Heating

11: 83 percent / PdCl₂; CuCl; O₂ / dimethylformamide; H₂O / 3 h / 20 °C

12: 78 percent / PDC / CH₂Cl₂ / 1.5 h / Heating

With dipyridinium dichromate; oxalyl dichloride; sulfuric acid; hydrogen; oxygen; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; sodium iodide; copper(l) chloride; palladium dichloride; palladium on barium sulfate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; butanone; 1: Substitution / 2: Alkylation / 3: Catalytic hydrogenation / 4: Oxidation / 5: Grignard reaction / 6: Alkylation / 7: Ring cleavage / 8: mesylation / 9: Elimination / 10: Ring cleavage / 11: Cyclization / 12: Oxidation;
DOI:10.1016/S0968-0896(99)00164-9

Reference yield:

: 250598-83-5
[(3aR,6R,6aS)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-methanol

: 250598-94-8
(3aR,5R,6R,6aR)-5-((S)-Benzyloxy-phenyl-methyl)-6-hydroxy-tetrahydro-furo[3,2-b]furan-2-one

Guidance literature:: Multi-step reaction with 11 steps

1: 26 percent / NaH / dimethylformamide / 0.5 h / 0 °C

2: 95 percent / H₂ / 10 percent Pd-BaSO₄ / methanol / 4 h

3: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1 h / -78 °C

4: 58 percent / tetrahydrofuran / 4 h / 0 °C

5: 90 percent / NaH / dimethylformamide / 0.5 h / 20 °C

6: 85 percent / AcOH / H₂O / 8 h / 20 °C

7: 85 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

8: 82 percent / NaI / butan-2-one / 12 h / Heating

9: 82 percent / 5 percent aq. H₂SO₄ / dioxane / 1 h / Heating

10: 83 percent / PdCl₂; CuCl; O₂ / dimethylformamide; H₂O / 3 h / 20 °C

11: 78 percent / PDC / CH₂Cl₂ / 1.5 h / Heating

With dipyridinium dichromate; oxalyl dichloride; sulfuric acid; hydrogen; oxygen; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; sodium iodide; copper(l) chloride; palladium dichloride; palladium on barium sulfate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; butanone; 1: Alkylation / 2: Catalytic hydrogenation / 3: Oxidation / 4: Grignard reaction / 5: Alkylation / 6: Ring cleavage / 7: mesylation / 8: Elimination / 9: Ring cleavage / 10: Cyclization / 11: Oxidation;
DOI:10.1016/S0968-0896(99)00164-9