(5R,6R)-6-((R)-1,2-dihydroxyethyl)-5-(4-methoxy benzyloxy)-5,6-dihydropyran-2-one

Base Information

Chemical Name:(5R,6R)-6-((R)-1,2-dihydroxyethyl)-5-(4-methoxy benzyloxy)-5,6-dihydropyran-2-one
CAS No.:1308247-27-9
Molecular Formula:C₁₅H₁₈O₆
Molecular Weight:294.304
Hs Code.:

Synonyms:(5R,6R)-6-((R)-1,2-dihydroxyethyl)-5-(4-methoxy benzyloxy)-5,6-dihydropyran-2-one

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Chemical Property of (5R,6R)-6-((R)-1,2-dihydroxyethyl)-5-(4-methoxy benzyloxy)-5,6-dihydropyran-2-one

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Technology Process of (5R,6R)-6-((R)-1,2-dihydroxyethyl)-5-(4-methoxy benzyloxy)-5,6-dihydropyran-2-one

There total 7 articles about (5R,6R)-6-((R)-1,2-dihydroxyethyl)-5-(4-methoxy benzyloxy)-5,6-dihydropyran-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: 94.0%

: 1308247-26-8
(5R,6S)-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(4-methoxybenzyloxy)-5,6-dihydropyran-2-one

: 1308247-27-9
(5R,6R)-6-((R)-1,2-dihydroxyethyl)-5-(4-methoxy benzyloxy)-5,6-dihydropyran-2-one

Guidance literature:: With DOWEX-50 resin H⁽¹⁺⁾-form; In methanol; at 20 ℃; for 6h;
DOI:10.1016/j.tet.2011.03.107

Reference yield:

: 1175536-43-2
(1S,2S)-1-(tert-butyldimethylsilyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-2-ol

: 1308247-27-9
(5R,6R)-6-((R)-1,2-dihydroxyethyl)-5-(4-methoxy benzyloxy)-5,6-dihydropyran-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 3 h / 20 °C

2: potassium tri-sec-butyl-borohydride / tetrahydrofuran; toluene / 6 h / -78 - -40 °C

3: sodium hydride / tetrahydrofuran / 0 - 20 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

5: triethylamine / dichloromethane / 0 - 20 °C

6: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / Reflux

7: DOWEX-50 resin H⁽¹⁺⁾-form / methanol / 6 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; sodium hydride; potassium tri-sec-butyl-borohydride; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1016/j.tet.2011.03.107

Reference yield:

: 1308247-23-5
(1S,2R)-1-(tert-butyldimethylsilyloxy)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-2-ol

: 1308247-27-9
(5R,6R)-6-((R)-1,2-dihydroxyethyl)-5-(4-methoxy benzyloxy)-5,6-dihydropyran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: sodium hydride / tetrahydrofuran / 0 - 20 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

3: triethylamine / dichloromethane / 0 - 20 °C

4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 24 h / Reflux

5: DOWEX-50 resin H⁽¹⁺⁾-form / methanol / 6 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tet.2011.03.107