(2R,4aR,8aS)-6-((3,4-dimethoxybenzyloxy)methyl)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine

Base Information

Chemical Name:(2R,4aR,8aS)-6-((3,4-dimethoxybenzyloxy)methyl)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine
CAS No.:904293-05-6
Molecular Formula:C₂₅H₂₉BrO₅
Molecular Weight:489.406
Hs Code.:

Synonyms:(2R,4aR,8aS)-6-((3,4-dimethoxybenzyloxy)methyl)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine

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Chemical Property of (2R,4aR,8aS)-6-((3,4-dimethoxybenzyloxy)methyl)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine

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Technology Process of (2R,4aR,8aS)-6-((3,4-dimethoxybenzyloxy)methyl)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine

There total 3 articles about (2R,4aR,8aS)-6-((3,4-dimethoxybenzyloxy)methyl)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine 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: 97.0%

: 904293-22-7
((2R,4aR,8aS)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxin-6-yl)methanol

: 7306-46-9
4-chloromethyl-1,2-dimethoxy-benzene

: 904293-05-6
(2R,4aR,8aS)-6-((3,4-dimethoxybenzyloxy)methyl)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1021/ol0608606

Reference yield:

: 904293-04-5
(2R,4aR,8aS)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine-6-carbaldehyde

: 904293-05-6
(2R,4aR,8aS)-6-((3,4-dimethoxybenzyloxy)methyl)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / NaBH₄ / methanol / 0.08 h / 0 °C

2: 97 percent / TBAI; NaH / dimethylformamide; tetrahydrofuran / 18 h / 20 °C

With sodium tetrahydroborate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ol0608606

Reference yield:

: 815577-88-9
(2R,4aR,8aS)-hexahydro-4a-methyl-2-phenylbenzo[d][1,3]dioxin-5-one

: 904293-05-6
(2R,4aR,8aS)-6-((3,4-dimethoxybenzyloxy)methyl)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / molecular sieves 4 Angstroem; PBr₃ / 4 h / 70 °C

2: 97 percent / NaBH₄ / methanol / 0.08 h / 0 °C

3: 97 percent / TBAI; NaH / dimethylformamide; tetrahydrofuran / 18 h / 20 °C

With sodium tetrahydroborate; 4 A molecular sieve; phosphorus tribromide; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Vilsmeier reaction;
DOI:10.1021/ol0608606