4-Hydroxy-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester

Base Information

• Chemical Name: 4-Hydroxy-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester
• CAS No.: 176850-50-3
• Molecular Formula: C₂₃H₂₆O₇
• Molecular Weight: 414.455

Synonyms:4-Hydroxy-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester

Chemical Property of 4-Hydroxy-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester

Chemical Property:

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Technology Process of 4-Hydroxy-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester

There total 3 articles about 4-Hydroxy-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-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: 92.0%

4-Oxo-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester (176850-44-5) → 4-Hydroxy-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester (176850-50-3)

Guidance literature:

With sodium tetrahydroborate; zinc(II) chloride; In tetrahydrofuran; at -78 ℃; for 0.166667h;

DOI:10.1039/p19960000593

Reference yield:

β-benzoylpropionyl chloride (53917-82-1) → 4-Hydroxy-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester (176850-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / pyridine / CHCl₃ / 3.5 h / Ambient temperature

2: 92 percent / ZnCl₂, NaBH₄ / tetrahydrofuran / 0.17 h

With pyridine; sodium tetrahydroborate; zinc(II) chloride; In tetrahydrofuran; chloroform;

DOI:10.1016/S0040-4020(97)10005-9

Reference yield:

(2S,3R,3aR,6R,6aR)-2-Benzyloxy-hexahydro-furo[3,2-b]furan-3,6-diol → 4-Hydroxy-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester (176850-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / pyridine / CHCl₃ / 3.5 h / Ambient temperature

2: 92 percent / ZnCl₂, NaBH₄ / tetrahydrofuran / 0.17 h

With pyridine; sodium tetrahydroborate; zinc(II) chloride; In tetrahydrofuran; chloroform;

DOI:10.1016/S0040-4020(97)10005-9

upstream raw materials:

4-Oxo-4-phenyl-butyric acid (2S,3R,3aS,6R,6aR)-2-benzyloxy-6-hydroxy-hexahydro-furo[3,2-b]furan-3-yl ester

β-benzoylpropionyl chloride

Downstream raw materials:

(R)-4-phenylbutyrolactone

(-)-(S)-5-phenyl-4,5-dihydrofuran-2(3H)-one

4-hydroxy-4-phenylbutanoic acid

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