Benzoic acid (3R,3aR,5R,6R,7R,7aS)-7-bromo-5,6-dihydroxy-6-methyl-octahydro-benzofuran-3-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (3R,3aR,5R,6R,7R,7aS)-7-bromo-5,6-dihydroxy-6-methyl-octahydro-benzofuran-3-ylmethyl ester
CAS No.:898801-02-0
Molecular Formula:C₁₇H₂₁BrO₅
Molecular Weight:385.255
Hs Code.:

Synonyms:Benzoic acid (3R,3aR,5R,6R,7R,7aS)-7-bromo-5,6-dihydroxy-6-methyl-octahydro-benzofuran-3-ylmethyl ester

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Chemical Property of Benzoic acid (3R,3aR,5R,6R,7R,7aS)-7-bromo-5,6-dihydroxy-6-methyl-octahydro-benzofuran-3-ylmethyl ester

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Technology Process of Benzoic acid (3R,3aR,5R,6R,7R,7aS)-7-bromo-5,6-dihydroxy-6-methyl-octahydro-benzofuran-3-ylmethyl ester

There total 11 articles about Benzoic acid (3R,3aR,5R,6R,7R,7aS)-7-bromo-5,6-dihydroxy-6-methyl-octahydro-benzofuran-3-ylmethyl 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: 92.0%

: 898801-01-9
Benzoic acid (3aR,4R,4aS,7R,7aR,8aR)-4-bromo-2,2,3a-trimethyl-octahydro-furo[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-ylmethyl ester

: 898801-02-0
Benzoic acid (3R,3aR,5R,6R,7R,7aS)-7-bromo-5,6-dihydroxy-6-methyl-octahydro-benzofuran-3-ylmethyl ester

Guidance literature:: With hydrogenchloride; In methanol; at 20 ℃;
DOI:10.1055/s-2006-939698

Reference yield:

: 898800-92-5
Acetic acid 2-((1R,5R)-5-hydroxy-4-methyl-cyclohex-3-enyl)-allyl ester

: 898801-02-0
Benzoic acid (3R,3aR,5R,6R,7R,7aS)-7-bromo-5,6-dihydroxy-6-methyl-octahydro-benzofuran-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 93 percent / MCPBA; NaHCO₃ / CH₂Cl₂

2.1: 97 percent / n-BuLi; acetyl bromide; AcOH / tetrahydrofuran

3.1: 95 percent / TsOH / CH₂Cl₂ / 40 °C

4.1: BH₃*SMe₂ / tetrahydrofuran

4.2: 89 percent / aq. NaOH; H₂O₂ / tetrahydrofuran

5.1: 95 percent / t-BuOK / dimethylformamide

6.1: 95 percent / NBS / tetrahydrofuran / 20 °C

7.1: 99 percent / pyridine / CH₂Cl₂

8.1: 92 percent / aq. HCl / methanol / 20 °C

With pyridine; hydrogenchloride; N-Bromosuccinimide; n-butyllithium; Acetyl bromide; dimethylsulfide borane complex; potassium tert-butylate; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2006-939698

Reference yield:

: 898800-93-6
Acetic acid 2-((1S,3S,5R,6R)-5-hydroxy-6-methyl-7-oxa-bicyclo[4.1.0]hept-3-yl)-allyl ester

: 898801-02-0
Benzoic acid (3R,3aR,5R,6R,7R,7aS)-7-bromo-5,6-dihydroxy-6-methyl-octahydro-benzofuran-3-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / n-BuLi; acetyl bromide; AcOH / tetrahydrofuran

2.1: 95 percent / TsOH / CH₂Cl₂ / 40 °C

3.1: BH₃*SMe₂ / tetrahydrofuran

3.2: 89 percent / aq. NaOH; H₂O₂ / tetrahydrofuran

4.1: 95 percent / t-BuOK / dimethylformamide

5.1: 95 percent / NBS / tetrahydrofuran / 20 °C

6.1: 99 percent / pyridine / CH₂Cl₂

7.1: 92 percent / aq. HCl / methanol / 20 °C

With pyridine; hydrogenchloride; N-Bromosuccinimide; n-butyllithium; Acetyl bromide; dimethylsulfide borane complex; potassium tert-butylate; toluene-4-sulfonic acid; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2006-939698