(2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal

Base Information

Chemical Name:(2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal
CAS No.:1391093-75-6
Molecular Formula:C₂₃H₄₀O₄Si
Molecular Weight:408.654
Hs Code.:

Synonyms:(2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal

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Chemical Property of (2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal

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Technology Process of (2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal

There total 7 articles about (2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal 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: 90.0%

: 1391093-72-3
(2R,3S,4S,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-(tert-butyl-dimethylsilyloxy)-5-methoxy-2,4-dimethylheptan-1-one

: 1391093-75-6
(2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.166667h; Inert atmosphere;
DOI:10.1016/j.tetlet.2012.05.103

Reference yield:

: 1391093-61-0
(2R,3S,4R,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-7-(benzyloxy)-3-hydroxy-5-methoxy-2,4-dimethylheptan-1-one

: 1391093-75-6
(2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal

Guidance literature:: Multi-step reaction with 2 steps

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

2: diisobutylaluminium hydride / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In dichloromethane;
DOI:10.1016/j.tetlet.2012.05.103

Reference yield:

: 1391093-66-5
((2R,3S)-5-(benzyloxy)-3-methoxy-2-methylpentyloxy)(tert-butyl)dimethylsilane

: 1391093-75-6
(2R,3S,4S,5S)-7-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-5-methoxy-2,4-dimethylheptanal

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / tetrahydrofuran; dimethyl sulfoxide / 3 h / 20 °C

3.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C

3.2: 0.33 h / 0 °C

3.3: 3 h / 0 °C

4.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C

5.1: diisobutylaluminium hydride / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; titanium tetrachloride; diisobutylaluminium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2012.05.103