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

Base Information

Chemical Name:(2R,3S,4R,5R)-4-benzyloxy-2-((tert-butyldimethylsilyloxy)methyl)-5-methyltetrahydrofuran-3-ol
CAS No.:1346433-76-8
Molecular Formula:C₁₉H₃₂O₄Si
Molecular Weight:352.546
Hs Code.:

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

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Chemical Property of (2R,3S,4R,5R)-4-benzyloxy-2-((tert-butyldimethylsilyloxy)methyl)-5-methyltetrahydrofuran-3-ol

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Technology Process of (2R,3S,4R,5R)-4-benzyloxy-2-((tert-butyldimethylsilyloxy)methyl)-5-methyltetrahydrofuran-3-ol

There total 2 articles about (2R,3S,4R,5R)-4-benzyloxy-2-((tert-butyldimethylsilyloxy)methyl)-5-methyltetrahydrofuran-3-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:

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

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1346433-86-0
(2S,3S,4R,5R)-4-benzyloxy-2-((tert-butyldimethylsilyloxy)methyl)-5-methyltetrahydrofuran-3-ol

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

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 ℃; Inert atmosphere;
DOI:10.1021/jo201570h

Reference yield:

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

: 1346433-86-0
(2S,3S,4R,5R)-4-benzyloxy-2-((tert-butyldimethylsilyloxy)methyl)-5-methyltetrahydrofuran-3-ol

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

Guidance literature:: Multi-step reaction with 2 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

With 1H-imidazole; potassium tert-butylate; In dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo201570h

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