Acetic acid (2R,3R,3aS,5R,6R,7S,7aS)-3-hydroxy-2-methoxy-5-phenyl-6-phenylselanyl-hexahydro-furo[3,2-b]pyran-7-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,3aS,5R,6R,7S,7aS)-3-hydroxy-2-methoxy-5-phenyl-6-phenylselanyl-hexahydro-furo[3,2-b]pyran-7-yl ester
CAS No.:1053642-13-9
Molecular Formula:C₂₂H₂₄O₆Se
Molecular Weight:463.389
Hs Code.:

Synonyms:Acetic acid (2R,3R,3aS,5R,6R,7S,7aS)-3-hydroxy-2-methoxy-5-phenyl-6-phenylselanyl-hexahydro-furo[3,2-b]pyran-7-yl ester

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Chemical Property of Acetic acid (2R,3R,3aS,5R,6R,7S,7aS)-3-hydroxy-2-methoxy-5-phenyl-6-phenylselanyl-hexahydro-furo[3,2-b]pyran-7-yl ester

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Technology Process of Acetic acid (2R,3R,3aS,5R,6R,7S,7aS)-3-hydroxy-2-methoxy-5-phenyl-6-phenylselanyl-hexahydro-furo[3,2-b]pyran-7-yl ester

There total 7 articles about Acetic acid (2R,3R,3aS,5R,6R,7S,7aS)-3-hydroxy-2-methoxy-5-phenyl-6-phenylselanyl-hexahydro-furo[3,2-b]pyran-7-yl ester 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: 41.0%

: 883860-04-6
Acetic acid (E)-(R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-allyl ester

: 5707-04-0
Phenylselenyl chloride

: 1053642-13-9
Acetic acid (2R,3R,3aS,5R,6R,7S,7aS)-3-hydroxy-2-methoxy-5-phenyl-6-phenylselanyl-hexahydro-furo[3,2-b]pyran-7-yl ester

Guidance literature:: With sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 19h;
DOI:10.1021/jo052025s

Reference yield:

: 643024-91-3
Benzoic acid (R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-ynyl ester

: 1053642-13-9
Acetic acid (2R,3R,3aS,5R,6R,7S,7aS)-3-hydroxy-2-methoxy-5-phenyl-6-phenylselanyl-hexahydro-furo[3,2-b]pyran-7-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 53 percent / BioRad 50 WX acidic resin / methanol; tetrahydrofuran / 19 h / 70 °C

2: 96 percent / 2,6-lutidine / CH₂Cl₂ / 3.5 h / 0 °C

3: lithium aluminum hydride / tetrahydrofuran / 3.5 h / 50 °C

4: 3.64 g / 4-DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

5: 92 percent / TBAF / tetrahydrofuran / 0 - 20 °C

6: 41 percent / sodium hydrogen carbonate / CH₂Cl₂ / 19 h / 20 °C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; BioRad 50 WX acidic resin; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo052025s

Reference yield:

: 883860-01-3
Benzoic acid (R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-prop-2-ynyl ester

: 1053642-13-9
Acetic acid (2R,3R,3aS,5R,6R,7S,7aS)-3-hydroxy-2-methoxy-5-phenyl-6-phenylselanyl-hexahydro-furo[3,2-b]pyran-7-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 3.5 h / 0 °C

2: lithium aluminum hydride / tetrahydrofuran / 3.5 h / 50 °C

3: 3.64 g / 4-DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

4: 92 percent / TBAF / tetrahydrofuran / 0 - 20 °C

5: 41 percent / sodium hydrogen carbonate / CH₂Cl₂ / 19 h / 20 °C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo052025s