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

Base Information

Chemical Name:(2R,4aR,8aS)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine-6-carbaldehyde
CAS No.:904293-04-5
Molecular Formula:C₁₆H₁₇BrO₃
Molecular Weight:337.213
Hs Code.:

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

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

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

There total 1 articles about (2R,4aR,8aS)-5-bromo-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine-6-carbaldehyde 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: 70.0%

: 68-12-2,33513-42-7
N,N-dimethyl-formamide

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

: 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

Guidance literature:: With 4 A molecular sieve; phosphorus tribromide; at 70 ℃; for 4h;
DOI:10.1021/ol0608606

Reference yield: 97.0%

: 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

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

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.0833333h;
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

: ((1R,2S,6S)-6-(benzyloxy)-2-((benzyloxy)methyl)-1-methyl-3-methylenecyclohexyl)methanol

Guidance literature:: Multi-step reaction with 14 steps

1.1: 97 percent / NaBH₄ / methanol / 0.08 h / 0 °C

2.1: 97 percent / TBAI; NaH / dimethylformamide; tetrahydrofuran / 18 h / 20 °C

3.1: t-BuLi / tetrahydrofuran; pentane / 0.25 h / -78 °C

3.2: tetrahydrofuran; pentane / 0.5 h / cooling

4.1: 95 percent / NaBH₄ / methanol; tetrahydrofuran / 0.25 h / 20 °C

5.1: 92 percent / NaH; TBAI / dimethylformamide; tetrahydrofuran / 8 h / 20 °C

6.1: 69 percent / diisobutylaluminum hydride / CH₂Cl₂; toluene / 7 h / 20 °C

7.1: 73 percent / DIPEA / CH₂Cl₂ / 0.17 h / 20 °C

8.1: 91 percent / DDQ; potassium phosphate buffer / CH₂Cl₂; 2-methyl-propan-2-ol / 1 h / 20 °C / pH 7

9.1: TEA / CH₂Cl₂ / 0.25 h / -95 °C

10.1: 46.5 mg / LiBr / tetrahydrofuran / 1 h / 20 °C

11.1: 90 percent / p-TsOH / acetone; H₂O / 3 h / 50 °C

12.1: 88 percent / 2 h / 100 °C

13.1: 97 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

14.1: 87 percent / LiAlH₄ / tetrahydrofuran / 1 h / -78 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; potassium phosphate buffer; TEA; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; pentane;
DOI:10.1021/ol0608606