3-((1R,4R,5R)-1,4-Dihydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-3-yl)-benzoic acid methyl ester

Base Information

Chemical Name:3-((1R,4R,5R)-1,4-Dihydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-3-yl)-benzoic acid methyl ester
CAS No.:862791-81-9
Molecular Formula:C₁₅H₁₄O₆
Molecular Weight:290.273
Hs Code.:

Synonyms:3-((1R,4R,5R)-1,4-Dihydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-3-yl)-benzoic acid methyl ester

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Chemical Property of 3-((1R,4R,5R)-1,4-Dihydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-3-yl)-benzoic acid methyl ester

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Technology Process of 3-((1R,4R,5R)-1,4-Dihydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-3-yl)-benzoic acid methyl ester

There total 6 articles about 3-((1R,4R,5R)-1,4-Dihydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-3-yl)-benzoic 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: 89.0%

: 862791-50-2
3-[(1R,4R,5R)-1,4-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-3-yl]-benzoic acid methyl ester

: 862791-81-9
3-((1R,4R,5R)-1,4-Dihydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-3-yl)-benzoic acid methyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h;
DOI:10.1021/jm0501836

Reference yield:

: 862791-08-0
(1S,3R,4R,5R)-3-benzyloxy-1,4-bis(tert-butyldimethylsilyloxy)cyclohexane-1,5-carbolactone

: 862791-81-9
3-((1R,4R,5R)-1,4-Dihydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-3-yl)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / H₂ / Pd(OH)2/C / methanol / 48 h / 20 °C

2.1: 95 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 5 h / 20 °C

3.1: potassium bis(trimethylsilyl)amide / dimethylformamide; toluene / 1 h / -78 °C

3.2: 80 percent / dimethylformamide; toluene / 15 h / -78 - 20 °C

4.1: 62 percent / (dba)3Pd₂*CHCl₃; Et₃N / tetrahydrofuran; CH₂Cl₂ / -78 - 20 °C

5.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; dipyridinium dichromate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Suzuki cross-coupling;
DOI:10.1021/jm0501836

Reference yield:

: 185810-83-7
(1S,3R,4R,5R)-3-benzyloxy-1,4-dihydroxycyclohexane-1,5-carbolactone

: 862791-81-9
3-((1R,4R,5R)-1,4-Dihydroxy-7-oxo-6-oxa-bicyclo[3.2.1]oct-2-en-3-yl)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

2.1: 99 percent / H₂ / Pd(OH)2/C / methanol / 48 h / 20 °C

3.1: 95 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 5 h / 20 °C

4.1: potassium bis(trimethylsilyl)amide / dimethylformamide; toluene / 1 h / -78 °C

4.2: 80 percent / dimethylformamide; toluene / 15 h / -78 - 20 °C

5.1: 62 percent / (dba)3Pd₂*CHCl₃; Et₃N / tetrahydrofuran; CH₂Cl₂ / -78 - 20 °C

6.1: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; dipyridinium dichromate; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 5.1: Suzuki cross-coupling;
DOI:10.1021/jm0501836