(((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)methoxy)(tert-butyl)dimethylsilane

Base Information

Chemical Name:(((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)methoxy)(tert-butyl)dimethylsilane
CAS No.:1346433-77-9
Molecular Formula:C₂₇H₄₀O₅Si
Molecular Weight:472.697
Hs Code.:

Synonyms:(((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)methoxy)(tert-butyl)dimethylsilane

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Chemical Property of (((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)methoxy)(tert-butyl)dimethylsilane

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Technology Process of (((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)methoxy)(tert-butyl)dimethylsilane

There total 3 articles about (((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)methoxy)(tert-butyl)dimethylsilane 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: 91.0%

: 1346433-76-8
(2R,3S,4R,5R)-4-benzyloxy-2-((tert-butyldimethylsilyloxy)methyl)-5-methyltetrahydrofuran-3-ol

: 2746-25-0
p-Methoxybenzyl bromide

: 1346433-77-9
(((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)methoxy)(tert-butyl)dimethylsilane

Guidance literature:: (2R,3S,4R,5R)-4-benzyloxy-2-((tert-butyldimethylsilyloxy)methyl)-5-methyltetrahydrofuran-3-ol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

p-Methoxybenzyl bromide; In tetrahydrofuran; mineral oil; at 20 ℃; Inert atmosphere;
DOI:10.1021/jo201570h

Reference yield:

: (3R,4R,5R)-4-(benzyloxy)-5-methyltetrahydro-2,3-furandiol

: 1346433-77-9
(((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)methoxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium tert-butylate / dimethyl sulfoxide / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 3 h / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 0 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

With 1H-imidazole; potassium tert-butylate; sodium hydride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; mineral oil;
DOI:10.1021/jo201570h

Reference yield:

: 1346433-75-7
(3S,4R,5R)-4-benzyloxy-2-(hydroxymethyl)-5-methyltetrahydrofuran-3-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1346433-77-9
(((2R,3S,4S,5R)-4-benzyloxy-3-(4-methoxybenzyloxy)-5-methyltetrahydrofuran-2-yl)methoxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / 0 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With 1H-imidazole; sodium hydride; In tetrahydrofuran; dichloromethane; mineral oil;
DOI:10.1021/jo201570h