(3aR,5S,6S,6aR)-5-((R)-benzyloxy(phenyl)methyl)-6-hydroxy-tetrahydrofuro[3,2-b]furan-2(5H)-one

Base Information

• Chemical Name: (3aR,5S,6S,6aR)-5-((R)-benzyloxy(phenyl)methyl)-6-hydroxy-tetrahydrofuro[3,2-b]furan-2(5H)-one
• CAS No.: 1262487-65-9
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.376

Synonyms:(3aR,5S,6S,6aR)-5-((R)-benzyloxy(phenyl)methyl)-6-hydroxy-tetrahydrofuro[3,2-b]furan-2(5H)-one

Chemical Property of (3aR,5S,6S,6aR)-5-((R)-benzyloxy(phenyl)methyl)-6-hydroxy-tetrahydrofuro[3,2-b]furan-2(5H)-one

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Technology Process of (3aR,5S,6S,6aR)-5-((R)-benzyloxy(phenyl)methyl)-6-hydroxy-tetrahydrofuro[3,2-b]furan-2(5H)-one

There total 1 articles about (3aR,5S,6S,6aR)-5-((R)-benzyloxy(phenyl)methyl)-6-hydroxy-tetrahydrofuro[3,2-b]furan-2(5H)-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: 81.0%

(3aR,5R,6S,6aS)-6-(allyloxy)-5-((R)-benzyloxy(phenyl)methyl)-tetrahydrofuro[3,2-b]furan-2(5H)-one (1262487-64-8) → (3aR,5S,6S,6aR)-5-((R)-benzyloxy(phenyl)methyl)-6-hydroxy-tetrahydrofuro[3,2-b]furan-2(5H)-one (1262487-65-9)

Guidance literature:

With palladium 10% on activated carbon; water; toluene-4-sulfonic acid; In methanol; at 80 ℃; for 12h;

DOI:10.1016/j.tetasy.2010.10.016

Reference yield: 86.0%

(3aR,5S,6S,6aR)-5-((R)-benzyloxy(phenyl)methyl)-6-hydroxy-tetrahydrofuro[3,2-b]furan-2(5H)-one (1262487-65-9) → (+)-goniofufurone (136778-39-7,144015-82-7,144829-37-8,129578-06-9)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2010.10.016

Reference yield:

(3aR,5S,6S,6aR)-5-((R)-benzyloxy(phenyl)methyl)-6-hydroxy-tetrahydrofuro[3,2-b]furan-2(5H)-one (1262487-65-9) + cinnamoyl 2,4,6-trichlorobenzoyl mixed anhydride (344414-37-5) → (2R,3S,3aS,6aR)-2-((R)-benzyloxy(phenyl)methyl)-5-oxo-hexahydrofuro[3,2-b]furan-3-yl cinnamate (1262487-66-0)

Guidance literature:

With dmap; In toluene; at 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2010.10.016

upstream raw materials:

(3aR,5R,6S,6aS)-6-(allyloxy)-5-((R)-benzyloxy(phenyl)methyl)-tetrahydrofuro[3,2-b]furan-2(5H)-one

Downstream raw materials:

(+)-goniofufurone

(2R,3S,3aS,6aR)-2-((R)-benzyloxy(phenyl)methyl)-5-oxo-hexahydrofuro[3,2-b]furan-3-yl cinnamate

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