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

Base Information

Chemical Name:((2R,4aR,8aS)-5-((benzyloxy)methyl)-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxin-6-yl)methanol
CAS No.:904293-26-1
Molecular Formula:C₂₄H₂₈O₄
Molecular Weight:380.484
Hs Code.:

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

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Chemical Property of ((2R,4aR,8aS)-5-((benzyloxy)methyl)-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxin-6-yl)methanol

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Technology Process of ((2R,4aR,8aS)-5-((benzyloxy)methyl)-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxin-6-yl)methanol

There total 7 articles about ((2R,4aR,8aS)-5-((benzyloxy)methyl)-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxin-6-yl)methanol 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%

: 904293-17-0
(2R,4aR,8aS)-6-((3,4-dimethoxybenzyloxy)methyl)-5-((benzyloxy)methyl)-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxine

: 904293-26-1
((2R,4aR,8aS)-5-((benzyloxy)methyl)-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxin-6-yl)methanol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; tert-butyl alcohol; at 20 ℃; for 0.5h; pH=7;
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

: 904293-26-1
((2R,4aR,8aS)-5-((benzyloxy)methyl)-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxin-6-yl)methanol

Guidance literature:: Multi-step reaction with 6 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: 82 percent / patassium phosphate buffer; DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 0.5 h / 20 °C / pH 7

With sodium tetrahydroborate; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; pentane;
DOI:10.1021/ol0608606

Reference yield:

: 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

: 904293-26-1
((2R,4aR,8aS)-5-((benzyloxy)methyl)-4a,7,8,8a-tetrahydro-4a-methyl-2-phenyl-4H-benzo[d][1,3]dioxin-6-yl)methanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 97 percent / TBAI; NaH / dimethylformamide; tetrahydrofuran / 18 h / 20 °C

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

2.2: tetrahydrofuran; pentane / 0.5 h / cooling

3.1: 95 percent / NaBH₄ / methanol; tetrahydrofuran / 0.25 h / 20 °C

4.1: 92 percent / NaH; TBAI / dimethylformamide; tetrahydrofuran / 8 h / 20 °C

5.1: 82 percent / patassium phosphate buffer; DDQ / CH₂Cl₂; 2-methyl-propan-2-ol / 0.5 h / 20 °C / pH 7

With sodium tetrahydroborate; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; pentane;
DOI:10.1021/ol0608606