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

Base Information

Chemical Name: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
CAS No.:112373-12-3
Molecular Formula:C₃₃H₃₉BrO₇Si
Molecular Weight:655.658
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 9 articles about 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 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: 82.0%

: 112373-11-2
4-Bromo-benzoic acid (4S,4aS,5S,8R,8aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-8-(tert-butyl-diphenyl-silanyloxy)-4a-hydroxy-2,2,7-trimethyl-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

: 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

Guidance literature:: In methanol; trifluoroacetic acid; at 22 ℃; for 30h;
DOI:10.1021/jo00238a047

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; sodium tetrahydroborate; 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:

: 110598-02-2
(4S,4aS,5R,8R,8aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-4a-hydroxy-2,2,7-trimethyl-8-triethylsilanyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxine-5-carbaldehyde

: 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

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / NaBH₄ / methanol / 0 °C

2: 73 percent / pyridine / 22 °C

3: 75 percent / pyridine hydrochloride / pyridine / 28 h / 22 °C

4: 93 percent / imidazole / dimethylformamide / 22 °C

5: 82 percent / trifluoroacetic acid; methanol / 30 h / 22 °C

With 1H-imidazole; sodium tetrahydroborate; pyridine hydrochloride; In pyridine; methanol; N,N-dimethyl-formamide; trifluoroacetic acid;
DOI:10.1021/jo00238a047