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

Base Information

• Chemical Name: 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
• CAS No.: 173613-48-4
• Molecular Formula: C₂₇H₃₉BrO₇Si
• Molecular Weight: 583.592
• Mol file: 173613-48-4.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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: 64.0%

4-Bromo-benzoic acid (4aR,5aS,8R,9S,10aS,11R,11aR)-9-(tert-butyl-dimethyl-silanyloxymethyl)-8-methanesulfonyloxy-2,2-dimethyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalen-11-yl ester (188050-73-9) → 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)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 100 ℃; for 58h;

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

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 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)

Guidance literature:

Multi-step reaction with 3 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

With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In 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-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-(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)

Guidance literature:

Multi-step reaction with 4 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

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

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

upstream raw materials:

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

tert-butyldimethylsilyl chloride

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

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