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

Base Information

• Chemical Name: 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-hydroxymethyl-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester
• CAS No.: 173613-34-8
• Molecular Formula: C₂₁H₂₅BrO₇
• Molecular Weight: 469.329

Synonyms:4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-hydroxymethyl-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

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

Chemical Property:

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

There total 6 articles about 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-hydroxymethyl-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-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: 94.0%

4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester (173613-48-4) → 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-hydroxymethyl-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester (173613-34-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(97)00071-9

Reference yield:

4-Bromo-benzoic acid (4aR,5aS,8R,9S,10aS,11R,11aR)-8-hydroxy-2,2-dimethyl-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester (173613-32-6) → 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-hydroxymethyl-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester (173613-34-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, CH₂Cl₂, -80 deg C, 15 min, 2.) 0 deg C, 4 h

2: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 20 h / Ambient temperature

3: 98 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) room temperature, 1.5 h

4: 64 percent / DBU / toluene / 58 h / 100 °C

5: 94 percent / n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

With dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4020(97)00071-9

Reference yield:

4-Bromo-benzoic acid (4aR,5aS,8R,9S,10aS,11R,11aR)-8-hydroxy-9-hydroxymethyl-2,2-dimethyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester (173613-47-3) → 4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-hydroxymethyl-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester (173613-34-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 20 h / Ambient temperature

2: 98 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) room temperature, 1.5 h

3: 64 percent / DBU / toluene / 58 h / 100 °C

4: 94 percent / n-Bu₄NF / tetrahydrofuran / 3 h / Ambient temperature

With dmap; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4020(97)00071-9

upstream raw materials:

4-Bromo-benzoic acid (4aR,5aS,9R,10aS,11R,11aR)-9-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

4-Bromo-benzoic acid (4aR,5aS,8R,9S,10aS,11R,11aR)-8-hydroxy-2,2-dimethyl-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

4-Bromo-benzoic acid (4aR,5aS,8R,9S,10aS,11R,11aR)-8-hydroxy-9-hydroxymethyl-2,2-dimethyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

4-Bromo-benzoic acid (4aR,5aS,8R,9S,10aS,11R,11aR)-9-(tert-butyl-dimethyl-silanyloxymethyl)-8-hydroxy-2,2-dimethyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester

Downstream raw materials:

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

C₃₁H₃₂Br₂O₉

(4aR,5aS,9R,10aS,11R,11aR)-11-Benzyloxymethoxy-9-((E)-(S)-3,4-bis-benzyloxymethoxy-but-1-enyl)-2,2-dimethyl-4,4a,5a,6,9,10a,11,11a-octahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

C₃₉H₄₀Br₂O₁₀

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