(3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol

Base Information

Chemical Name:(3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol
CAS No.:130698-44-1
Molecular Formula:C₁₀H₁₅BrO₄
Molecular Weight:279.131
Hs Code.:

Synonyms:(3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol

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Chemical Property of (3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol

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Technology Process of (3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol

There total 1 articles about (3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol 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:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 130669-72-6,137501-12-3
(3aS,4R,5S,7aS)-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol

: 74-88-4
methyl iodide

: 130698-44-1
(3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol

Guidance literature:: triisopropylsilyl trifluoromethanesulfonate; (3aS,4R,5S,7aS)-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol; With 2,6-dimethylpyridine; In dichloromethane; at -78 - 22 ℃; for 3h; Inert atmosphere;

methyl iodide; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 22 ℃; for 2h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 22 ℃; for 2h; Inert atmosphere;
DOI:10.1021/acs.joc.7b01062

Reference yield: 74.0%

: 100-39-0
benzyl bromide

: 130698-44-1
(3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol

: C₁₇H₂₁BrO₄

Guidance literature:: (3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 18 ℃; for 0.5h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 18 ℃; for 1h;

Reference yield: 45.0%

: 4-hydroxy-3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde

: 130698-44-1
(3aS,4R,5S,7aS)-7-bromo-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo-[d][1,3]dioxol-4-ol

: 4-hydroxy-3-((3aR,6S,7R,7aS)-7-hydroxy-6-methoxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxol-4-yl)-5-methoxybenzaldehyde

Guidance literature:: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; triethylamine; In tetrahydrofuran; water; at 66 ℃; for 2h; Inert atmosphere;
DOI:10.1021/acs.joc.7b01062