(4R,5S)-5-((4S,5S)-5-((R)-(tertbutyldimethyl-silyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxydihydrofuran-2(3H)-one

Base Information

Chemical Name:(4R,5S)-5-((4S,5S)-5-((R)-(tertbutyldimethyl-silyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxydihydrofuran-2(3H)-one
CAS No.:1311946-23-2
Molecular Formula:C₂₂H₃₄O₆Si
Molecular Weight:422.594
Hs Code.:

Synonyms:(4R,5S)-5-((4S,5S)-5-((R)-(tertbutyldimethyl-silyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxydihydrofuran-2(3H)-one

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Chemical Property of (4R,5S)-5-((4S,5S)-5-((R)-(tertbutyldimethyl-silyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxydihydrofuran-2(3H)-one

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Technology Process of (4R,5S)-5-((4S,5S)-5-((R)-(tertbutyldimethyl-silyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxydihydrofuran-2(3H)-one

There total 10 articles about (4R,5S)-5-((4S,5S)-5-((R)-(tertbutyldimethyl-silyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxydihydrofuran-2(3H)-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: 87.0%

: 1311946-21-0
(4R,5S)-4-(benzyloxy)-5-((4S,5S)-5-((R)-(tert-butyldimethylsilyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)dihydrofuran-2(3H)-one

: 1311946-23-2
(4R,5S)-5-((4S,5S)-5-((R)-(tertbutyldimethyl-silyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxydihydrofuran-2(3H)-one

Guidance literature:: With hydrogen; palladium(II) hydroxide; In ethyl acetate; for 24h; under 760.051 Torr;
DOI:10.1016/j.tet.2011.04.014

Reference yield:

: 1311946-08-3
(4R,5R)-4-(benzyloxy)-5-vinyldihydrofuran-2(3h)-one

: 1311946-23-2
(4R,5S)-5-((4S,5S)-5-((R)-(tertbutyldimethyl-silyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxydihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 5 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 8 h / Inert atmosphere; Reflux

2: 1H-imidazole / dichloromethane / 8 h / 0 - 20 °C

3: osmium(VIII) oxide; AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 24 h / 0 °C

4: camphorsulfonic acid / acetone / 2 h

5: hydrogen; palladium(II) hydroxide / ethyl acetate / 24 h / 760.05 Torr

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; methanesulfonamide; AD-mix β; hydrogen; palladium(II) hydroxide; In dichloromethane; water; ethyl acetate; acetone; tert-butyl alcohol; 1: olefin cross metathesis reaction;
DOI:10.1016/j.tet.2011.04.014

Reference yield:

: C₁₅H₂₀O₉S₂

: 1311946-23-2
(4R,5S)-5-((4S,5S)-5-((R)-(tertbutyldimethyl-silyloxy)(phenyl)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxydihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 6 steps

1: sodium iodide / butanone / 12 h / Reflux

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 8 h / Inert atmosphere; Reflux

3: 1H-imidazole / dichloromethane / 8 h / 0 - 20 °C

4: osmium(VIII) oxide; AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 24 h / 0 °C

5: camphorsulfonic acid / acetone / 2 h

6: hydrogen; palladium(II) hydroxide / ethyl acetate / 24 h / 760.05 Torr

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; methanesulfonamide; AD-mix β; hydrogen; palladium(II) hydroxide; sodium iodide; In dichloromethane; water; ethyl acetate; acetone; butanone; tert-butyl alcohol; 2: olefin cross metathesis reaction;
DOI:10.1016/j.tet.2011.04.014