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

Base Information

• Chemical Name: (R)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)propan-2-yl 3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)propanoate
• CAS No.: 869293-30-1
• Molecular Formula: C₂₉H₄₈O₆Si₂
• Molecular Weight: 548.868
• Mol file: 869293-30-1.mol

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

Chemical Property of (R)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)propan-2-yl 3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)propan-2-yl 3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)propanoate

There total 18 articles about (R)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)propan-2-yl 3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)propanoate 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: 81.0%

(R)-6-[(R)-2-hydroxypropyl]-5,6-dihydro-2H-pyran-2-one (942292-99-1) + 3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid (116511-71-8) → (R)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)propan-2-yl 3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)propanoate (869293-30-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;

DOI:10.1055/s-0034-1378784

Reference yield:

(5R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-ol → (R)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)propan-2-yl 3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)propanoate (869293-30-1)

Guidance literature:

Multi-step reaction with 5 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

With dmap; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; 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:

(R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one (869293-25-4) → (R)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)propan-2-yl 3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)propanoate (869293-30-1)

Guidance literature:

Multi-step reaction with 6 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

With dmap; sodium tetrahydroborate; cerium(III) chloride; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; 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

upstream raw materials:

(S)-6-((R)-2-Hydroxy-propyl)-3,6-dihydro-pyran-2-one

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

(S)-6-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-3,6-dihydro-pyran-2-one

3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid

Downstream raw materials:

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