4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11S,11aR)-9-hydroxymethyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-11-yl ester

Base Information

• Chemical Name: 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11S,11aR)-9-hydroxymethyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-11-yl ester
• CAS No.: 250660-95-8
• Molecular Formula: C₂₀H₂₃BrO₆
• Molecular Weight: 439.303

Synonyms:

Chemical Property of 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11S,11aR)-9-hydroxymethyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-11-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11S,11aR)-9-hydroxymethyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-11-yl ester

There total 24 articles about 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11S,11aR)-9-hydroxymethyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-11-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:

4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11S,11aR)-9-(tert-butyl-dimethyl-silanyloxymethyl)-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-11-yl ester → 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11S,11aR)-9-hydroxymethyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-11-yl ester (250660-95-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1055/s-1999-3646

Reference yield:

(2S,3R,4R,5S,6R)-2-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (173613-44-0) → 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11S,11aR)-9-hydroxymethyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-11-yl ester (250660-95-8)

Guidance literature:

Multi-step reaction with 24 steps

1.1: PPTs / CH₂Cl₂ / 20 °C

2.1: NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

3.1: DIBAL / CH₂Cl₂ / -20 °C

4.1: pyridine; DMAP / CH₂Cl₂ / 20 °C

5.1: 18-crown-6 / dimethylformamide / 80 °C

6.1: DDQ; H₂O / CH₂Cl₂ / 20 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

8.1: DIBAL / CH₂Cl₂ / -78 °C

9.1: (TMS)2NNa / tetrahydrofuran / 0 °C

10.1: 9-BBN / tetrahydrofuran

10.2: H₂O₂; NaOH / tetrahydrofuran

11.1: pyridine / 20 °C

12.1: 91 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

13.1: imidazole / dimethylformamide / 20 °C

14.1: H₂ / Pd(OH)2 / ethanol; ethyl acetate

15.1: pyridine; DMAP / 0 °C

16.1: dppb / Pd(dba)2 / tetrahydrofuran / 65 °C

17.1: DIBALH / CH₂Cl₂ / -78 °C

19.1: O₃ / CH₂Cl₂; methanol / -78 °C

20.1: NaBH₄ / -78 - 0 °C

21.1: Et₃N; DMAP / CH₂Cl₂ / 20 °C

22.1: Et₃N / CH₂Cl₂ / 0 - 20 °C

23.1: DBU / toluene / 100 °C

24.1: TBAF / tetrahydrofuran / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; 18-crown-6 ether; tetrabutyl ammonium fluoride; water; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,4-di(diphenylphosphino)-butane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 1.1: Condensation / 2.1: Etherification / 3.1: Reduction / 4.1: Tosylation / 5.1: Substitution / 6.1: Hydrolysis / 7.1: Etherification / 8.1: Reduction / 9.1: Condensation / 10.1: Addition / 10.2: Oxidation / 11.1: Tosylation / 12.1: Cyclization / 13.1: Etherification / 14.1: Hydrogenolysis / 15.1: Acylation / 16.1: Substitution / 17.1: Reduction / 19.1: Oxidation / 20.1: Reduction / 21.1: Etherification / 22.1: Substitution / 23.1: Elimination / 24.1: desilylation;

DOI:10.1055/s-1999-3646

Reference yield:

3-((2S,3S,4S,4aR,8aR)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propan-1-ol (250660-89-0) → 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11S,11aR)-9-hydroxymethyl-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-11-yl ester (250660-95-8)

Guidance literature:

Multi-step reaction with 12 steps

1: imidazole / dimethylformamide / 20 °C

2: H₂ / Pd(OH)2 / ethanol; ethyl acetate

3: pyridine; DMAP / 0 °C

4: dppb / Pd(dba)2 / tetrahydrofuran / 65 °C

5: DIBALH / CH₂Cl₂ / -78 °C

7: O₃ / CH₂Cl₂; methanol / -78 °C

8: NaBH₄ / -78 - 0 °C

9: Et₃N; DMAP / CH₂Cl₂ / 20 °C

10: Et₃N / CH₂Cl₂ / 0 - 20 °C

11: DBU / toluene / 100 °C

12: TBAF / tetrahydrofuran / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 1,4-di(diphenylphosphino)-butane; palladium dihydroxide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Etherification / 2: Hydrogenolysis / 3: Acylation / 4: Substitution / 5: Reduction / 7: Oxidation / 8: Reduction / 9: Etherification / 10: Substitution / 11: Elimination / 12: desilylation;

DOI:10.1055/s-1999-3646

upstream raw materials:

(2S,3R,4R,5S,6R)-2-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

3-((2S,3S,4S,4aR,8aR)-3,4-Bis-benzyloxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propan-1-ol

4-Bromo-benzoic acid (4aR,5aS,8R,9S,10aS,11S,11aR)-8-hydroxy-9-vinyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-11-yl ester

(2S,3R,4S,4aS,8aR)-3-Allyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-octahydro-pyrano[3,2-b]pyran-4-ol

Downstream raw materials:

4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11S,11aR)-9-[(E)-3-hydroxy-4-(4-methoxy-benzyloxy)-but-1-enyl]-2,3,4,4a,5a,6,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-11-yl ester

C₃₀H₃₀Br₂O₈

C₃₀H₃₀Br₂O₈

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