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

Base Information

• Chemical Name: Benzoic acid (1S,4R,5R)-1-hydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester
• CAS No.: 215370-45-9
• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.262
• Mol file: 215370-45-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about Benzoic acid (1S,4R,5R)-1-hydroxy-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: 97.0%

(1R,3S,4S,5R)-3-bromo-1-hydroxy-7-oxo-6-oxabicyclo[3.2.1]oct-4-yl benzoate (105539-78-4) → Benzoic acid (1S,4R,5R)-1-hydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester (215370-45-9)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 4h; Heating;

DOI:10.1016/S0957-4166(98)00284-5

Reference yield: 89.0%

methanol (67-56-1) + Benzoic acid (1S,4R,5R)-1-hydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester (215370-45-9) → (1S,3R,4R)-1-methoxycarbonyl-cyclohexane-1,3,4-triol (215370-46-0)

Guidance literature:

With potassium carbonate; for 1h; Ambient temperature;

DOI:10.1016/S0957-4166(98)00284-5

Reference yield:

Benzoic acid (1S,4R,5R)-1-hydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-4-yl ester (215370-45-9) → (3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-cyclohex-1-enecarboxylic acid methyl ester (215370-51-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / K₂CO₃ / 1 h / Ambient temperature

2: 1.) imidazole, 2.) pyridinium chlorochromate, 3 A molecular sieves, pyridine, 3.) POCl₃, pyridine

3: 0.8 g / NaBH₄ / methanol / 0.08 h / 0 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; 3 A molecular sieve; potassium carbonate; pyridinium chlorochromate; trichlorophosphate; In methanol;

DOI:10.1016/S0957-4166(98)00284-5

upstream raw materials:

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

Downstream raw materials:

(1S,3R,4R)-1-methoxycarbonyl-cyclohexane-1,3,4-triol

(3S,4R)-4-hydroxy-1-methoxycarbonyl-3-methyloxy-cyclohex-1-ene

(1S,2S,3R,4R)-1-hydroxymethyl-4-triethylsilyloxy-3-methoxy-1-cyclohexane-1,2-diol

(R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-cyclohex-1-enecarboxylic acid methyl ester