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

Base Information

• Chemical Name: Acetic acid (E)-(R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-allyl ester
• CAS No.: 883860-04-6
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331
• Mol file: 883860-04-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about Acetic acid (E)-(R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-allyl 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%

Acetic acid (E)-(R)-1-[(2R,3R,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-tetrahydro-furan-2-yl]-3-phenyl-allyl ester (883860-03-5) → Acetic acid (E)-(R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-allyl ester (883860-04-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/jo052025s

Reference yield:

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) → Acetic acid (E)-(R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-allyl ester (883860-04-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 3.5 h / 0 °C

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

3: 3.64 g / 4-DMAP; triethylamine / CH₂Cl₂ / 0 - 20 °C

4: 92 percent / TBAF / tetrahydrofuran / 0 - 20 °C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

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 (E)-(R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-allyl ester (883860-04-6)

Guidance literature:

Multi-step reaction with 5 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

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; BioRad 50 WX acidic resin; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo052025s

upstream raw materials:

Acetic acid (E)-(R)-1-[(2R,3R,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-tetrahydro-furan-2-yl]-3-phenyl-allyl ester

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

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

Benzoic acid (R)-1-[(2R,3R,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-tetrahydro-furan-2-yl]-3-phenyl-prop-2-ynyl ester

Downstream raw materials:

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