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

Base Information

Chemical Name:4-Bromo-benzoic acid (4S,4aS,5S,8R,8aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4a-hydroxy-2,2,7-trimethyl-8-triethylsilanyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester
CAS No.:110598-04-4
Molecular Formula:C₃₂H₅₃BrO₇Si₂
Molecular Weight:685.844
Hs Code.:

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

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

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Chemical Property of 4-Bromo-benzoic acid (4S,4aS,5S,8R,8aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4a-hydroxy-2,2,7-trimethyl-8-triethylsilanyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

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Technology Process of 4-Bromo-benzoic acid (4S,4aS,5S,8R,8aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4a-hydroxy-2,2,7-trimethyl-8-triethylsilanyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

There total 9 articles about 4-Bromo-benzoic acid (4S,4aS,5S,8R,8aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4a-hydroxy-2,2,7-trimethyl-8-triethylsilanyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-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: 73.0%

: 586-75-4
4-chlorobenzoyl chloride

: 110598-03-3
(4S,4aS,5S,8R,8aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-hydroxymethyl-2,2,7-trimethyl-8-triethylsilanyloxy-8,8a-dihydro-5H-benzo[1,3]dioxin-4a-ol

: 110598-04-4
4-Bromo-benzoic acid (4S,4aS,5S,8R,8aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4a-hydroxy-2,2,7-trimethyl-8-triethylsilanyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

Guidance literature:: In pyridine; at 22 ℃;
DOI:10.1021/jo00238a047

Reference yield:

: 994-30-9
triethylsilyl chloride

: 110598-04-4
4-Bromo-benzoic acid (4S,4aS,5S,8R,8aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4a-hydroxy-2,2,7-trimethyl-8-triethylsilanyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / imidazole / dimethylformamide / 0.08 h / 22 °C

2: 76 percent / DDQ, H₂O / CH₂Cl₂ / 22 °C

3: 51 percent / (CH₃)2SO, (COCl)2 / 10 h / -60 °C

4: 85 percent / NaBH₄ / methanol / 0 °C

5: 73 percent / pyridine / 22 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; water; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00238a047

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 110598-04-4
4-Bromo-benzoic acid (4S,4aS,5S,8R,8aR)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4a-hydroxy-2,2,7-trimethyl-8-triethylsilanyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxin-5-ylmethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) H⁺, 2.) NaIO₄, 3.) NaBH₄, 4.) DMAP, Et₃N, 5.) DMSO, (COCl)2

2: 1.) LDA

3: 83 percent / imidazole / dimethylformamide / 0.08 h / 22 °C

4: 76 percent / DDQ, H₂O / CH₂Cl₂ / 22 °C

5: 51 percent / (CH₃)2SO, (COCl)2 / 10 h / -60 °C

6: 85 percent / NaBH₄ / methanol / 0 °C

7: 73 percent / pyridine / 22 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium periodate; oxalyl dichloride; water; hydrogen cation; dimethyl sulfoxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00238a047