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

Base Information

• Chemical Name: Benzoic acid (R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-prop-2-ynyl ester
• CAS No.: 883860-01-3
• Molecular Formula: C₂₁H₂₀O₆
• Molecular Weight: 368.386
• Mol file: 883860-01-3.mol

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

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

There total 3 articles about Benzoic acid (R)-1-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-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: 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:

benzoyl chloride (98-88-4) → 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:

Multi-step reaction with 2 steps

1: 92 percent / 4-DMAP; triethylamine / CH₂Cl₂ / 2 h / 0 - 20 °C

2: 53 percent / BioRad 50 WX acidic resin / methanol; tetrahydrofuran / 19 h / 70 °C

With dmap; BioRad 50 WX acidic resin; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo052025s

Reference yield:

(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-((2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-3-phenyl-prop-2-ynyl ester (883860-01-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / 4-DMAP; triethylamine / CH₂Cl₂ / 2 h / 0 - 20 °C

2: 53 percent / BioRad 50 WX acidic resin / methanol; tetrahydrofuran / 19 h / 70 °C

With dmap; BioRad 50 WX acidic resin; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo052025s

upstream raw materials:

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

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:

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

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,3aS,5R,6R,7S,7aS)-3-hydroxy-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