((3R,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-yl)methanol

Base Information

• Chemical Name: ((3R,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-yl)methanol
• CAS No.: 1643718-31-3
• Molecular Formula: C₂₃H₂₇BrO₂
• Molecular Weight: 415.37
• Mol file: 1643718-31-3.mol

Synonyms:((3R,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-yl)methanol

Chemical Property of ((3R,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-yl)methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3R,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-yl)methanol

There total 3 articles about ((3R,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-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: 90.0%

2,2-bis(2-(o-tolyl)allyl)propane-1,3-diol (1643718-20-0) → ((3R,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-yl)methanol (1643718-31-3)

Guidance literature:

With N-bromophthalimide; C₃₂H₃₉N₃O₃S; In hexane; chloroform; at -60 ℃; for 12h; enantioselective reaction; Inert atmosphere; Molecular sieve; Darkness;

DOI:10.1002/anie.201310136

Reference yield:

dimethyl 2,2-bis(2-(o-tolyl)allyl)malonate (1643718-57-3) → ((3R,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-yl)methanol (1643718-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 25 °C / Inert atmosphere

2: N-bromophthalimide; C₃₂H₃₉N₃O₃S / chloroform; hexane / 12 h / -60 °C / Inert atmosphere; Molecular sieve; Darkness

With lithium aluminium tetrahydride; N-bromophthalimide; C₃₂H₃₉N₃O₃S; In tetrahydrofuran; hexane; chloroform;

DOI:10.1002/anie.201310136

Reference yield:

1-(3-bromoprop-1-en-2-yl)-2-methylbenzene (445235-57-4) → ((3R,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-yl)methanol (1643718-31-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 25 °C / Inert atmosphere

1.2: 12 h / Inert atmosphere; Reflux

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 25 °C / Inert atmosphere

3.1: N-bromophthalimide; C₃₂H₃₉N₃O₃S / chloroform; hexane / 12 h / -60 °C / Inert atmosphere; Molecular sieve; Darkness

With lithium aluminium tetrahydride; N-bromophthalimide; C₃₂H₃₉N₃O₃S; sodium hydride; In tetrahydrofuran; hexane; chloroform; mineral oil;

DOI:10.1002/anie.201310136

upstream raw materials:

dimethyl 2,2-bis(2-(o-tolyl)allyl)malonate

2,2-bis(2-(o-tolyl)allyl)propane-1,3-diol

1-(3-bromoprop-1-en-2-yl)-2-methylbenzene

Downstream raw materials:

(3S,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-carboxylic acid

(3S,5R,8S)-3,8-bis(bromomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one

(3S,5R,8S)-8-(bromomethyl)-3-(iodomethyl)-3,8-di-o-tolyl-2,7-dioxaspiro[4.4]nonan-1-one

(3S,5S)-5-(bromomethyl)-5-(o-tolyl)-3-(2-(o-tolyl)allyl)tetrahydrofuran-3-carbaldehyde