Benzoic acid (R)-1-[(1R,5R,7S,8R)-7-bromomethyl-8-(2,2-dimethyl-propionyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-ylmethyl]-prop-2-ynyl ester

Base Information

Chemical Name:Benzoic acid (R)-1-[(1R,5R,7S,8R)-7-bromomethyl-8-(2,2-dimethyl-propionyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-ylmethyl]-prop-2-ynyl ester
CAS No.:242809-41-2
Molecular Formula:C₂₇H₃₃BrO₅
Molecular Weight:517.46
Hs Code.:

Benzoic acid (R)-1-[(1R,5R,7S,8R)-7-bromomethyl-8-(2,2-dimethyl-propionyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-ylmethyl]-prop-2-ynyl ester

Synonyms:Benzoic acid (R)-1-[(1R,5R,7S,8R)-7-bromomethyl-8-(2,2-dimethyl-propionyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-ylmethyl]-prop-2-ynyl ester

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Chemical Property of Benzoic acid (R)-1-[(1R,5R,7S,8R)-7-bromomethyl-8-(2,2-dimethyl-propionyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-ylmethyl]-prop-2-ynyl ester

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Technology Process of Benzoic acid (R)-1-[(1R,5R,7S,8R)-7-bromomethyl-8-(2,2-dimethyl-propionyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-ylmethyl]-prop-2-ynyl ester

There total 8 articles about Benzoic acid (R)-1-[(1R,5R,7S,8R)-7-bromomethyl-8-(2,2-dimethyl-propionyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-ylmethyl]-prop-2-ynyl 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: 90.0%

: 65-85-0,8013-63-6
benzoic acid

: 242809-37-6
2,2-Dimethyl-propionic acid (1R,5R,7S,8R)-7-bromomethyl-5-((S)-2-hydroxy-but-3-ynyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-8-ylmethyl ester

: 242809-41-2
Benzoic acid (R)-1-[(1R,5R,7S,8R)-7-bromomethyl-8-(2,2-dimethyl-propionyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-ylmethyl]-prop-2-ynyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate;
DOI:10.1021/ja990183t

Reference yield:

: 172172-73-5
[(1R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-1-hydroxy-5-isopropenyl-2-methyl-cyclohex-2-enyl]-acetonitrile

: 242809-41-2
Benzoic acid (R)-1-[(1R,5R,7S,8R)-7-bromomethyl-8-(2,2-dimethyl-propionyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-ylmethyl]-prop-2-ynyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / pyridinium bromide perbromide / pyridine / 0.33 h

2: DIBAL / toluene / 2 h

3: toluene; tetrahydrofuran / 0.5 h

4: 41 percent / imidazole / dimethylformamide / 2 h / 60 °C

5: 99 percent / TBAF

6: 75 percent

7: 90 percent / DEAD, Ph₃P

With 1H-imidazole; tetrabutyl ammonium fluoride; pyridinium hydrobromide perbromide; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja990183t

Reference yield:

: 172172-74-6
[(1R,5R,7S,8R)-7-Bromomethyl-8-(tert-butyl-dimethyl-silanyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-yl]-acetonitrile

: 242809-41-2
Benzoic acid (R)-1-[(1R,5R,7S,8R)-7-bromomethyl-8-(2,2-dimethyl-propionyloxymethyl)-4,7-dimethyl-6-oxa-bicyclo[3.2.1]oct-3-en-5-ylmethyl]-prop-2-ynyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: DIBAL / toluene / 2 h

2: toluene; tetrahydrofuran / 0.5 h

3: 41 percent / imidazole / dimethylformamide / 2 h / 60 °C

4: 99 percent / TBAF

5: 75 percent

6: 90 percent / DEAD, Ph₃P

With 1H-imidazole; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja990183t