(2S,3S,4S,5S)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-3,5-dimethylhexanal

Base Information

Chemical Name:(2S,3S,4S,5S)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-3,5-dimethylhexanal
CAS No.:1269830-02-5
Molecular Formula:C₂₉H₄₄O₅Si
Molecular Weight:500.751
Hs Code.:

Synonyms:(2S,3S,4S,5S)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-3,5-dimethylhexanal

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Chemical Property of (2S,3S,4S,5S)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-3,5-dimethylhexanal

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Technology Process of (2S,3S,4S,5S)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-3,5-dimethylhexanal

There total 9 articles about (2S,3S,4S,5S)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-3,5-dimethylhexanal 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: 84.0%

: (2S,3S,4S,5S)-1-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-6-[(R)-tert-butylsulfinyl]-5-(4-methoxybenzyloxy)-2,4-dimethylhexane

: 1269830-02-5
(2S,3S,4S,5S)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-3,5-dimethylhexanal

Guidance literature:: With 2,4,6-trimethyl-pyridine; trifluoroacetic anhydride; In acetonitrile; at 0 ℃; for 0.25h;
DOI:10.1039/c0ob00491j

Reference yield:

: (3R,4S,5S)-6-(benzyloxy)-1-[(R)-tert-butylsulfinyl]-4-hydroxy-3,5-dimethylhexan-2-one

: 1269830-02-5
(2S,3S,4S,5S)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-3,5-dimethylhexanal

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 3 h / -78 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C

2.2: 4 h / 0 °C

3.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C

4.1: 2,4,6-trimethyl-pyridine; trifluoroacetic anhydride / acetonitrile / 0.25 h / 0 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; sodium hydride; diisobutylaluminium hydride; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 4.1: Pummerer reaction;
DOI:10.1039/c0ob00491j

Reference yield:

: (2S,3R,4S,5S)-6-(benzyloxy)-1-[(R)-tert-butylsulfinyl]-3,5-dimethylhexane-2,4-diol

: 1269830-02-5
(2S,3S,4S,5S)-6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-3,5-dimethylhexanal

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C

1.2: 4 h / 0 °C

2.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C

3.1: 2,4,6-trimethyl-pyridine; trifluoroacetic anhydride / acetonitrile / 0.25 h / 0 °C

With 2,6-dimethylpyridine; 2,4,6-trimethyl-pyridine; sodium hydride; trifluoroacetic anhydride; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 3.1: Pummerer reaction;
DOI:10.1039/c0ob00491j