(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-furan-2-ol

Base Information

Chemical Name:(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-furan-2-ol
CAS No.:1601460-55-2
Molecular Formula:C₂₆H₃₇BrO₅Si
Molecular Weight:537.566
Hs Code.:

Synonyms:(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-furan-2-ol

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Chemical Property of (3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-furan-2-ol

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Technology Process of (3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-furan-2-ol

There total 3 articles about (3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-furan-2-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:

: 869732-13-8
3-(benzyloxy)-5-bromo-2-methoxybenzaldehyde

: 1601460-55-2
(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-furan-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere

2.1: phosphorus tribromide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

3.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere

With sodium tetrahydroborate; phosphorus tribromide; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1016/j.tet.2014.03.020

Reference yield:

: 1601460-51-8
1-(benzyloxy)-5-bromo-3-(bromomethyl)-2-methoxybenzene

: 1601460-55-2
(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-furan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere

With diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; toluene;
DOI:10.1016/j.tet.2014.03.020

Reference yield:

: 1601460-53-0
(3-(benzyloxy)-5-bromo-2-methoxyphenyl)methanol

: 1601460-55-2
(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-furan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: phosphorus tribromide / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere

With phosphorus tribromide; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tet.2014.03.020