(1R,4R,5R)-1,4-dihydroxy-3-[(1R)-1-hydroxy-2-phenylacetyl]cyclohex-2-en-1,5-carbolactone

Base Information

Chemical Name:(1R,4R,5R)-1,4-dihydroxy-3-[(1R)-1-hydroxy-2-phenylacetyl]cyclohex-2-en-1,5-carbolactone
CAS No.:1598377-50-4
Molecular Formula:C₁₅H₁₆O₅
Molecular Weight:276.289
Hs Code.:

Synonyms:(1R,4R,5R)-1,4-dihydroxy-3-[(1R)-1-hydroxy-2-phenylacetyl]cyclohex-2-en-1,5-carbolactone

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Chemical Property of (1R,4R,5R)-1,4-dihydroxy-3-[(1R)-1-hydroxy-2-phenylacetyl]cyclohex-2-en-1,5-carbolactone

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Technology Process of (1R,4R,5R)-1,4-dihydroxy-3-[(1R)-1-hydroxy-2-phenylacetyl]cyclohex-2-en-1,5-carbolactone

There total 3 articles about (1R,4R,5R)-1,4-dihydroxy-3-[(1R)-1-hydroxy-2-phenylacetyl]cyclohex-2-en-1,5-carbolactone 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: 26.0%

: 1598377-48-0
(1R,4R,5R)-1,4-dihydroxy-3-(2-benzylacetyl)cyclohex-2-en-1,5-carbolactone

: 1598377-49-1
(1R,4R,5R)-1,4-dihydroxy-3-[(1S)-1-hydroxy-2-phenylacetyl]cyclohex-2-en-1,5-carbolactone

: 1598377-50-4
(1R,4R,5R)-1,4-dihydroxy-3-[(1R)-1-hydroxy-2-phenylacetyl]cyclohex-2-en-1,5-carbolactone

Guidance literature:: With cerium(III) chloride heptahydrate; sodium tris(acetoxy)borohydride; In tetrahydrofuran; methanol; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jm500175z

Reference yield:

: 53317-09-2
9-benzyl-9-borabicyclo[3.3.1]nonane

: 1598377-50-4
(1R,4R,5R)-1,4-dihydroxy-3-[(1R)-1-hydroxy-2-phenylacetyl]cyclohex-2-en-1,5-carbolactone

Guidance literature:: Multi-step reaction with 3 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; tetrahydrofuran / 4 h / 55 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / Inert atmosphere

3: cerium(III) chloride heptahydrate; sodium tris(acetoxy)borohydride / methanol; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; In tetrahydrofuran; methanol; water; 1: |Suzuki Coupling;
DOI:10.1021/jm500175z

Reference yield:

: 862791-05-7
(1R,4S,5R)-1,4-di(tert-butyldimethylsilyloxy)cyclohex-2-en-1,5-carbolactone 3-(trifluoromethane sulphonate)

: 1598377-50-4
(1R,4R,5R)-1,4-dihydroxy-3-[(1R)-1-hydroxy-2-phenylacetyl]cyclohex-2-en-1,5-carbolactone

Guidance literature:: Multi-step reaction with 3 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; tetrahydrofuran / 4 h / 55 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / Inert atmosphere

3: cerium(III) chloride heptahydrate; sodium tris(acetoxy)borohydride / methanol; tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; sodium tris(acetoxy)borohydride; In tetrahydrofuran; methanol; water; 1: |Suzuki Coupling;
DOI:10.1021/jm500175z