Acetic acid (2R,3R,3aR,6S,7R,7aS)-6,7-dihydroxy-5-oxo-2-phenyl-hexahydro-furo[3,2-b]pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,3aR,6S,7R,7aS)-6,7-dihydroxy-5-oxo-2-phenyl-hexahydro-furo[3,2-b]pyran-3-yl ester
• CAS No.: 242150-07-8
• Molecular Formula: C₁₅H₁₆O₇
• Molecular Weight: 308.288
• Mol file: 242150-07-8.mol

Synonyms:Acetic acid (2R,3R,3aR,6S,7R,7aS)-6,7-dihydroxy-5-oxo-2-phenyl-hexahydro-furo[3,2-b]pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,3aR,6S,7R,7aS)-6,7-dihydroxy-5-oxo-2-phenyl-hexahydro-furo[3,2-b]pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,3aR,6S,7R,7aS)-6,7-dihydroxy-5-oxo-2-phenyl-hexahydro-furo[3,2-b]pyran-3-yl ester

There total 2 articles about Acetic acid (2R,3R,3aR,6S,7R,7aS)-6,7-dihydroxy-5-oxo-2-phenyl-hexahydro-furo[3,2-b]pyran-3-yl 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: 75.0%

(2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate (65409-11-2) → Acetic acid (2R,3R,3aR,6S,7R,7aS)-6,7-dihydroxy-5-oxo-2-phenyl-hexahydro-furo[3,2-b]pyran-3-yl ester (242150-07-8)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; water; In acetone; at 20 ℃; for 1.5h;

DOI:10.1021/np990089q

Reference yield:

goniothalenol (65408-91-5) → Acetic acid (2R,3R,3aR,6S,7R,7aS)-6,7-dihydroxy-5-oxo-2-phenyl-hexahydro-furo[3,2-b]pyran-3-yl ester (242150-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / pyridine / 1 h / 20 °C

2: 75 percent / H₂O; OsO₄; NMO / acetone / 1.5 h / 20 °C

With pyridine; osmium(VIII) oxide; N-methyl-2-indolinone; water; In acetone; 1: Acetylation / 2: Addition;

DOI:10.1021/np990089q

Reference yield: 54.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + Acetic acid (2R,3R,3aR,6S,7R,7aS)-6,7-dihydroxy-5-oxo-2-phenyl-hexahydro-furo[3,2-b]pyran-3-yl ester (242150-07-8) → Acetic acid (3aS,5aR,6R,7R,8aS,8bS)-4-oxo-7-phenyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-6-yl ester

Guidance literature:

With chloro-trimethyl-silane; triethylamine; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1021/np990089q

upstream raw materials:

(2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate

goniothalenol