(R)-1-((R)-6-oxo-3,6-dihydro-2H-2-pyranyl)propan-2-yl 3-(3,4-dihydroxyphenyl)propionate

Base Information

Chemical Name:(R)-1-((R)-6-oxo-3,6-dihydro-2H-2-pyranyl)propan-2-yl 3-(3,4-dihydroxyphenyl)propionate
CAS No.:869293-31-2
Molecular Formula:C₁₇H₂₀O₆
Molecular Weight:320.342
Hs Code.:

Synonyms:(R)-1-((R)-6-oxo-3,6-dihydro-2H-2-pyranyl)propan-2-yl 3-(3,4-dihydroxyphenyl)propionate

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Chemical Property of (R)-1-((R)-6-oxo-3,6-dihydro-2H-2-pyranyl)propan-2-yl 3-(3,4-dihydroxyphenyl)propionate

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Technology Process of (R)-1-((R)-6-oxo-3,6-dihydro-2H-2-pyranyl)propan-2-yl 3-(3,4-dihydroxyphenyl)propionate

There total 18 articles about (R)-1-((R)-6-oxo-3,6-dihydro-2H-2-pyranyl)propan-2-yl 3-(3,4-dihydroxyphenyl)propionate 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: 88.0%

: 869293-30-1
(R)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)propan-2-yl 3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)propanoate

: 869293-31-2
(R)-1-((R)-6-oxo-3,6-dihydro-2H-2-pyranyl)propan-2-yl 3-(3,4-dihydroxyphenyl)propionate

Guidance literature:: With tetrabutyl ammonium fluoride; benzoic acid; at 20 ℃; for 1h;
DOI:10.1055/s-0034-1378784

Reference yield:

: (5R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-ol

: 869293-31-2
(R)-1-((R)-6-oxo-3,6-dihydro-2H-2-pyranyl)propan-2-yl 3-(3,4-dihydroxyphenyl)propionate

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / DCC; DMAP

2: Grubbs catalyst II / CH₂Cl₂ / 12 h / 40 °C

3: 98 percent / HF / H₂O; acetonitrile

4: DCC; DMAP

5: DBU / CHCl₃

6: 79 percent / benzoic acid; TBAF

With dmap; hydrogen fluoride; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; benzoic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; chloroform; water; acetonitrile;
DOI:10.1016/j.tetlet.2005.08.164

Reference yield:

: 869293-25-4
(R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one

: 869293-31-2
(R)-1-((R)-6-oxo-3,6-dihydro-2H-2-pyranyl)propan-2-yl 3-(3,4-dihydroxyphenyl)propionate

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / NaBH₄; CeCl₃

2: 83 percent / DCC; DMAP

3: Grubbs catalyst II / CH₂Cl₂ / 12 h / 40 °C

4: 98 percent / HF / H₂O; acetonitrile

5: DCC; DMAP

6: DBU / CHCl₃

7: 79 percent / benzoic acid; TBAF

With dmap; sodium tetrahydroborate; cerium(III) chloride; hydrogen fluoride; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; benzoic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; chloroform; water; acetonitrile; 1: Luche reaction;
DOI:10.1016/j.tetlet.2005.08.164