(S)-3-(4-Hydroxy-phenyl)-3-((3S,3aS,6S,6aR)-3,3a,6-trihydroxy-2-oxo-hexahydro-furo[3,2-b]furan-3-yl)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-3-(4-Hydroxy-phenyl)-3-((3S,3aS,6S,6aR)-3,3a,6-trihydroxy-2-oxo-hexahydro-furo[3,2-b]furan-3-yl)-propionic acid methyl ester
• CAS No.: 113119-34-9
• Molecular Formula: C₁₆H₁₈O₉
• Molecular Weight: 354.314
• Mol file: 113119-34-9.mol

Synonyms:

Chemical Property of (S)-3-(4-Hydroxy-phenyl)-3-((3S,3aS,6S,6aR)-3,3a,6-trihydroxy-2-oxo-hexahydro-furo[3,2-b]furan-3-yl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(4-Hydroxy-phenyl)-3-((3S,3aS,6S,6aR)-3,3a,6-trihydroxy-2-oxo-hexahydro-furo[3,2-b]furan-3-yl)-propionic acid methyl ester

There total 3 articles about (S)-3-(4-Hydroxy-phenyl)-3-((3S,3aS,6S,6aR)-3,3a,6-trihydroxy-2-oxo-hexahydro-furo[3,2-b]furan-3-yl)-propionic acid methyl 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: 47.0%

methyl 3-hydroxy-3-(p-hydroxyphenyl)propionate (113119-30-5) + ascorbic acid (50-81-7,98966-42-8) → aglycone of dilaspirolactone (113119-31-6) + (S)-3-(4-Hydroxy-phenyl)-3-((3S,3aS,6S,6aR)-3,3a,6-trihydroxy-2-oxo-hexahydro-furo[3,2-b]furan-3-yl)-propionic acid methyl ester (113119-34-9,113216-06-1)

Guidance literature:

In water; at 50 ℃; for 72h;

DOI:10.1021/jo00242a037

Reference yield:

4-(trimethylsiloxy)benzaldehyde (1012-12-0) → (S)-3-(4-Hydroxy-phenyl)-3-((3S,3aS,6S,6aR)-3,3a,6-trihydroxy-2-oxo-hexahydro-furo[3,2-b]furan-3-yl)-propionic acid methyl ester (113119-34-9,113216-06-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA, 3.) NH₄Cl/H₂O / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, -78 deg C, 1 h, 3.) room temp., THF, hexane, 6 h

2: 47 percent / H₂O / 72 h / 50 °C

With water; ammonium chloride; lithium diisopropyl amide; In water;

DOI:10.1021/jo00242a037

Reference yield:

methyl 3-hydroxy-3-(p-hydroxyphenyl)propionate (113119-30-5) + isoascorbic acid (89-65-6,98966-42-8) → aglycone of dilaspirolactone (113119-31-6) + (S)-3-(4-Hydroxy-phenyl)-3-((3S,3aS,6S,6aR)-3,3a,6-trihydroxy-2-oxo-hexahydro-furo[3,2-b]furan-3-yl)-propionic acid methyl ester (113119-34-9,113216-06-1)

Guidance literature:

at 50 ℃; for 3h; Product distribution; various times and temp.;

DOI:10.1016/S0040-4039(00)96146-X

upstream raw materials:

methyl 3-hydroxy-3-(p-hydroxyphenyl)propionate

isoascorbic acid

ascorbic acid

4-(trimethylsiloxy)benzaldehyde

Downstream raw materials:

Sawaranin

4-episawaranin