Benzoic acid (R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-ynyl ester

Base Information

• Chemical Name: Benzoic acid (R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-ynyl ester
• CAS No.: 643024-91-3
• Molecular Formula: C₂₄H₂₄O₆
• Molecular Weight: 408.451
• Mol file: 643024-91-3.mol

Synonyms:Benzoic acid (R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-ynyl ester

Chemical Property of Benzoic acid (R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-ynyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-ynyl ester

There total 1 articles about Benzoic acid (R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-ynyl ester 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: 92.0%

benzoyl chloride (98-88-4) + (R)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-yn-1-ol (643024-90-2) → Benzoic acid (R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-ynyl ester (643024-91-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1021/jo052025s

Reference yield: 53.0%

Benzoic acid (R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-ynyl ester (643024-91-3) → Benzoic acid (R)-1-((2S,3S,4R,5S)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-prop-2-ynyl ester + Benzoic acid (R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-prop-2-ynyl ester (883860-01-3)

Guidance literature:

With BioRad 50 WX acidic resin; In tetrahydrofuran; methanol; at 70 ℃; for 19h;

DOI:10.1021/jo052025s

Reference yield:

Benzoic acid (R)-1-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-ynyl ester (643024-91-3) → Acetic acid (R)-1-((2R,3R,4R,6S)-4-acetoxy-3-hydroxy-6-phenyl-tetrahydro-pyran-2-yl)-2-oxo-ethyl ester

Guidance literature:

Multi-step reaction with 9 steps

1: 53 percent / BioRad 50 WX acidic resin / methanol; tetrahydrofuran / 19 h / 70 °C

2: 96 percent / 2,6-lutidine / CH₂Cl₂ / 3.5 h / 0 °C

3: lithium aluminum hydride / tetrahydrofuran / 3.5 h / 50 °C

4: 3.64 g / 4-DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

5: 92 percent / TBAF / tetrahydrofuran / 0 - 20 °C

6: 41 percent / sodium hydrogen carbonate / CH₂Cl₂ / 19 h / 20 °C

7: 92 percent / 4-DMAP; triethylamine / CH₂Cl₂ / 0.83 h / 0 °C

8: 90 percent / AIBN; tris(trimethylsilyl)silane / toluene / 15 h / 110 °C

9: periodic acid / RuCl₃ / acetonitrile

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; BioRad 50 WX acidic resin; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; periodic acid; triethylamine; ruthenium trichloride; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

DOI:10.1021/jo052025s

upstream raw materials:

benzoyl chloride

(R)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-phenyl-prop-2-yn-1-ol

Downstream raw materials:

Benzoic acid (R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-prop-2-ynyl ester

Acetic acid (E)-(R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-allyl ester

Acetic acid (2R,3R,3aR,5S,7R,7aR)-7-acetoxy-2-methoxy-5-phenyl-hexahydro-furo[3,2-b]pyran-3-yl ester

Acetic acid (2R,3R,3aS,5R,6R,7S,7aS)-3-hydroxy-2-methoxy-5-phenyl-6-phenylselanyl-hexahydro-furo[3,2-b]pyran-7-yl ester