(2S,3R,4R)-3-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-2-(p-toluenesulfonyloxy)-hept-6-ene

Base Information

Chemical Name:(2S,3R,4R)-3-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-2-(p-toluenesulfonyloxy)-hept-6-ene
CAS No.:1268616-19-8
Molecular Formula:C₂₉H₄₄O₇SSi
Molecular Weight:564.816
Hs Code.:

Synonyms:(2S,3R,4R)-3-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-2-(p-toluenesulfonyloxy)-hept-6-ene

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Chemical Property of (2S,3R,4R)-3-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-2-(p-toluenesulfonyloxy)-hept-6-ene

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Technology Process of (2S,3R,4R)-3-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-2-(p-toluenesulfonyloxy)-hept-6-ene

There total 6 articles about (2S,3R,4R)-3-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-2-(p-toluenesulfonyloxy)-hept-6-ene 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: 94.0%

: 1268616-26-7
C₂₂H₃₈O₅Si

: 98-59-9
p-toluenesulfonyl chloride

: 1268616-19-8
(2S,3R,4R)-3-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-2-(p-toluenesulfonyloxy)-hept-6-ene

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1016/j.tetasy.2010.11.005

Reference yield:

: 100906-42-1
2-O-benzyl-3,4-O-isopropylidene-L-threose

: 1268616-19-8
(2S,3R,4R)-3-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-2-(p-toluenesulfonyloxy)-hept-6-ene

Guidance literature:: Multi-step reaction with 5 steps

1.1: magnesium bromide ethyl etherate / dichloromethane / 2 h / -78 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / methanol / 12 h / 20 °C / Inert atmosphere

3.2: 0.17 h

4.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere

5.1: dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; pyridinium p-toluenesulfonate; magnesium bromide ethyl etherate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Keck allylation;
DOI:10.1016/j.tetasy.2010.11.005

Reference yield:

: 1268616-18-7
(2S,3R,4R)-3-(benzyloxy)-4-(methoxymethoxy)hept-6-ene-1,2-diol

: 1268616-19-8
(2S,3R,4R)-3-(benzyloxy)-1-(tert-butyldimethylsilyloxy)-4-(methoxymethoxy)-2-(p-toluenesulfonyloxy)-hept-6-ene

Guidance literature:: Multi-step reaction with 2 steps

1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 12 h / 0 - 20 °C / Inert atmosphere

2: dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetasy.2010.11.005