(3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Base Information

Chemical Name:(3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene
CAS No.:115404-48-3
Molecular Formula:C₂₂H₃₁BrO
Molecular Weight:391.392
Hs Code.:

Synonyms:(3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

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Chemical Property of (3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

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Technology Process of (3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

There total 13 articles about (3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene 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:

: 115333-56-7
(4aR,6S,8aS)-(+)-3,4,4a,5,6,7,8,8a-octahydro-6-benzyloxy-1-hydroxymethyl-2,5,5,8a-tetramethylnaphthalene

: 115404-48-3
(3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: With methanesulfonyl chloride; triethylamine; lithium bromide; Yield given. Multistep reaction; 1.) CH₂Cl₂, -60 deg C, 30 min; 2.) CH₂Cl₂-THF, -60 deg C then -20 deg C 45 min;
DOI:10.1016/S0040-4020(01)81631-8

Reference yield:

: 115333-57-8
Methanesulfonic acid (4aR,6S,8aS)-6-benzyloxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester

: 115404-48-3
(3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: With lithium bromide; In tetrahydrofuran; dichloromethane; at -20 ℃; for 1h; Yield given;

Reference yield:

: 115333-55-6
Methyl (4aR,6S,8aS)-6-(benzyloxy)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene-1-carboxylate

: 115404-48-3
(3S,4aR,8aS)-3-Benzyloxy-8-bromomethyl-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / DIBAL / toluene / 0.5 h / -78 °C

2: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

3: LiBr / tetrahydrofuran; CH₂Cl₂ / 1 h / -20 °C

With diisobutylaluminium hydride; triethylamine; lithium bromide; In tetrahydrofuran; dichloromethane; toluene;