(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one

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Chemical Name:(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one
CAS No.:1601460-54-1
Molecular Formula:C₂₆H₃₅BrO₅Si
Molecular Weight:535.55
Hs Code.:

Synonyms:(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one

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Chemical Property of (3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one

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Technology Process of (3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one

There total 3 articles about (3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one 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%

: 62396-80-9
(5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one

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

: 1601460-54-1
(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one

Guidance literature:: (5S)-(5-tert-butyldimethylsilyloxymethyl)furan-2(5H)-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

1-(benzyloxy)-5-bromo-3-(bromomethyl)-2-methoxybenzene; In tetrahydrofuran; at -78 ℃; for 0.5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2014.03.020

Reference yield:

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

: 1601460-54-1
(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

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

: 1601460-54-1
(3R,5S)-3-(3-(benzyloxy)-5-bromo-2-methoxybenzyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 2 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

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