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

Base Information

Chemical Name: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
CAS No.:173613-32-6
Molecular Formula:C₂₂H₂₇BrO₇
Molecular Weight:483.356
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 1 articles about 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 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,6S,7S,8R,8aR)-2,2-dimethyl-6-(3-oxo-propyl)-7-((Z)-3-tributylstannanyl-propenyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

: 173613-32-6
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

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -90 ℃; for 0.833333h;
DOI:10.1016/S0040-4020(97)00071-9

Reference yield:

: 173613-32-6
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,9R,10aS,11R,11aR)-9-[(E)-4-(4-methoxy-benzyloxy)-3-oxo-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

Guidance literature:: Multi-step reaction with 7 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

6: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / Ambient temperature

7: benzene / 1.5 h / Ambient temperature

With dmap; sodium tetrahydroborate; tetrabutyl ammonium fluoride; Dess-Martin periodane; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; toluene; benzene;
DOI:10.1016/S0040-4020(97)00071-9

Reference yield:

: 173613-32-6
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

: 188050-74-0
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

Guidance literature:: Multi-step reaction with 8 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

6: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / Ambient temperature

7: benzene / 1.5 h / Ambient temperature

8: CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -60 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; Dess-Martin periodane; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;
DOI:10.1016/S0040-4020(97)00071-9