(2R,3S,4R)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methylpentane-1,4-diol

Base Information

Chemical Name:(2R,3S,4R)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methylpentane-1,4-diol
CAS No.:1262137-92-7
Molecular Formula:C₂₀H₃₆O₅Si
Molecular Weight:384.588
Hs Code.:

Synonyms:(2R,3S,4R)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methylpentane-1,4-diol

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Chemical Property of (2R,3S,4R)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methylpentane-1,4-diol

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Technology Process of (2R,3S,4R)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methylpentane-1,4-diol

There total 4 articles about (2R,3S,4R)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methylpentane-1,4-diol 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: 89.0%

: 1262137-91-6
(3S,4S,5R)-4-((tert-butyldimethylsilyl)oxy)-5-(((4-methoxybenzyl)oxy)methyl)-3-methyldihydrofuran-2(3H)-one

: 1262137-92-7
(2R,3S,4R)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methylpentane-1,4-diol

Guidance literature:: With sodium tetrahydroborate; water; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tetlet.2011.12.020

Reference yield:

: 139426-88-3
<4S,3(2S,3R)>-4-benzyl-3-(3-hydroxy-2-methyl-4-pentenoyl)-2-oxazolidinone

: 1262137-92-7
(2R,3S,4R)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methylpentane-1,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-dimethylpyridine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 10 h / 20 °C / Inert atmosphere

3: 10-camphorsufonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere

4: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

With 2,6-dimethylpyridine; osmium(VIII) oxide; lithium aluminium tetrahydride; 10-camphorsufonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1002/ejoc.201001097

Reference yield:

: 519176-52-4
(S)-4-benzyl-3-{(2S,3R)-3-[(tert-butyldimethylsilyl)oxy]-2-methylpent-4-enoyl}oxazolidin-2-one

: 1262137-92-7
(2R,3S,4R)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2-methylpentane-1,4-diol

Guidance literature:: Multi-step reaction with 3 steps

1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 10 h / 20 °C / Inert atmosphere

2: 10-camphorsufonic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere

3: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

With osmium(VIII) oxide; lithium aluminium tetrahydride; 10-camphorsufonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1002/ejoc.201001097