4-Bromo-benzoic acid (3S,3aS,4S,7R,7aR)-7-(tert-butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

Base Information

Chemical Name:4-Bromo-benzoic acid (3S,3aS,4S,7R,7aR)-7-(tert-butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester
CAS No.:112348-96-6
Molecular Formula:C₃₃H₃₇BrO₆Si
Molecular Weight:637.643
Hs Code.:

4-Bromo-benzoic acid (3S,3aS,4S,7R,7aR)-7-(tert-butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

Synonyms:4-Bromo-benzoic acid (3S,3aS,4S,7R,7aR)-7-(tert-butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

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Chemical Property of 4-Bromo-benzoic acid (3S,3aS,4S,7R,7aR)-7-(tert-butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

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Technology Process of 4-Bromo-benzoic acid (3S,3aS,4S,7R,7aR)-7-(tert-butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

There total 10 articles about 4-Bromo-benzoic acid (3S,3aS,4S,7R,7aR)-7-(tert-butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-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: 71.0%

: 112373-12-3
4-Bromo-benzoic acid (1S,4R,5R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-((S)-1,2-dihydroxy-ethyl)-5,6-dihydroxy-3-methyl-cyclohex-2-enylmethyl ester

: 112348-96-6
4-Bromo-benzoic acid (3S,3aS,4S,7R,7aR)-7-(tert-butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

Guidance literature:: With 2,4,6-triisopropylphenylsulfonyl chloride; In pyridine; at 22 ℃; for 23h;
DOI:10.1021/jo00238a047

Reference yield:

: (Z)-5-(4-Methoxy-benzyloxy)-2-methyl-pent-2-enal

: 112348-96-6
4-Bromo-benzoic acid (3S,3aS,4S,7R,7aR)-7-(tert-butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) LDA

2: 83 percent / imidazole / dimethylformamide / 0.08 h / 22 °C

3: 76 percent / DDQ, H₂O / CH₂Cl₂ / 22 °C

4: 51 percent / (CH₃)2SO, (COCl)2 / 10 h / -60 °C

5: 85 percent / NaBH₄ / methanol / 0 °C

6: 73 percent / pyridine / 22 °C

7: 75 percent / pyridine hydrochloride / pyridine / 28 h / 22 °C

8: 93 percent / imidazole / dimethylformamide / 22 °C

9: 82 percent / trifluoroacetic acid; methanol / 30 h / 22 °C

10: 71 percent / 2,4,6-(i-C₃H₇)3C₆H₂SO₂Cl / pyridine / 23 h / 22 °C

With 1H-imidazole; sodium tetrahydroborate; 2,4,6-triisopropylphenylsulfonyl chloride; oxalyl dichloride; water; pyridine hydrochloride; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; trifluoroacetic acid;
DOI:10.1021/jo00238a047

Reference yield:

: 110598-00-0
(4S,6R)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-6-((Z)-(R)-5-hydroxy-2-methyl-1-triethylsilanyloxy-pent-2-enyl)-2,2-dimethyl-[1,3]dioxan-5-one

: 112348-96-6
4-Bromo-benzoic acid (3S,3aS,4S,7R,7aR)-7-(tert-butyl-diphenyl-silanyloxy)-3,3a-dihydroxy-6-methyl-2,3,3a,4,7,7a-hexahydro-benzofuran-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 51 percent / (CH₃)2SO, (COCl)2 / 10 h / -60 °C

2: 85 percent / NaBH₄ / methanol / 0 °C

3: 73 percent / pyridine / 22 °C

4: 75 percent / pyridine hydrochloride / pyridine / 28 h / 22 °C

5: 93 percent / imidazole / dimethylformamide / 22 °C

6: 82 percent / trifluoroacetic acid; methanol / 30 h / 22 °C

7: 71 percent / 2,4,6-(i-C₃H₇)3C₆H₂SO₂Cl / pyridine / 23 h / 22 °C

With 1H-imidazole; sodium tetrahydroborate; 2,4,6-triisopropylphenylsulfonyl chloride; oxalyl dichloride; pyridine hydrochloride; dimethyl sulfoxide; In pyridine; methanol; N,N-dimethyl-formamide; trifluoroacetic acid;
DOI:10.1021/jo00238a047