Benzoic acid (1S,3S,4R,5R)-1-hydroxy-3-(3-hydroxy-propyl)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester

Base Information

• Chemical Name: Benzoic acid (1S,3S,4R,5R)-1-hydroxy-3-(3-hydroxy-propyl)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester
• CAS No.: 618888-62-3
• Molecular Formula: C₁₇H₂₀O₆
• Molecular Weight: 320.342
• Mol file: 618888-62-3.mol

Synonyms:Benzoic acid (1S,3S,4R,5R)-1-hydroxy-3-(3-hydroxy-propyl)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester

Chemical Property of Benzoic acid (1S,3S,4R,5R)-1-hydroxy-3-(3-hydroxy-propyl)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,3S,4R,5R)-1-hydroxy-3-(3-hydroxy-propyl)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester

There total 1 articles about Benzoic acid (1S,3S,4R,5R)-1-hydroxy-3-(3-hydroxy-propyl)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-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: 31.0%

(1S,3S,4R,5R)-3-allyl-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate (183474-89-7) → Benzoic acid (1S,3S,4R,5R)-1-hydroxy-3-(3-hydroxy-propyl)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester (618888-62-3)

Guidance literature:

(1S,3S,4R,5R)-3-allyl-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate; With borane-THF; In tetrahydrofuran; at 0 ℃; for 1h;

With sodium perborate; In tetrahydrofuran; at 20 ℃; for 2h; Further stages.;

DOI:10.1039/b301731a

Reference yield: 98.0%

methanol (67-56-1) + Benzoic acid (1S,3S,4R,5R)-1-hydroxy-3-(3-hydroxy-propyl)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester (618888-62-3) → methyl (1S,3R,4R,5S)-5-(3'-hydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate (618888-64-5)

Guidance literature:

With sodium methylate; at 20 ℃; for 2h;

DOI:10.1039/b301731a

Reference yield:

Benzoic acid (1S,3S,4R,5R)-1-hydroxy-3-(3-hydroxy-propyl)-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester (618888-62-3) → (1S,3R,4R,5S)-1,3,4-Trihydroxy-5-(3-hydroxy-propyl)-cyclohexanecarboxylic acid

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaOMe / 2 h / 20 °C

2: 65 percent / aq. NaOH / 2 h / 20 °C / pH 12

With sodium hydroxide; sodium methylate;

DOI:10.1039/b301731a

upstream raw materials:

(1S,3S,4R,5R)-3-allyl-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate

Downstream raw materials:

methyl (1S,3R,4R,5S)-5-(3'-hydroxypropyl)-1,3,4-trihydroxycyclohexane-1-carboxylate