(2S,3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethylnon-6-ene-2,3-diol

Base Information

Chemical Name:(2S,3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethylnon-6-ene-2,3-diol
CAS No.:942133-23-5
Molecular Formula:C₂₅H₄₄O₅Si
Molecular Weight:452.707
Hs Code.:

Synonyms:(2S,3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethylnon-6-ene-2,3-diol

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Chemical Property of (2S,3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethylnon-6-ene-2,3-diol

Chemical Property:

Purity/Quality:

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Hazard Codes:

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Useful:

Technology Process of (2S,3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethylnon-6-ene-2,3-diol

There total 6 articles about (2S,3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethylnon-6-ene-2,3-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:

: 942133-22-4
(2S,4R,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate

: 942133-23-5
(2S,3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethylnon-6-ene-2,3-diol

: (2S,3S,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethylnon-6-ene-2,3-diol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at -78 - 20 ℃; for 76h; Title compound not separated from byproducts.;
DOI:10.1021/ja071461o

Reference yield:

: 942133-07-5
(E)-5-(4-methoxybenzyloxy)-3-methylpent-2-enal

: 942133-23-5
(2S,3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethylnon-6-ene-2,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: chlorodicyclohexylborane; Me₂NEt / diethyl ether; hexane / -78 - 0 °C

1.2: diethyl ether; hexane / 19 h / -78 - -22 °C

2.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - -40 °C

3.1: LiBH₄ / tetrahydrofuran / 76 h / -78 - 20 °C

With 2,6-dimethylpyridine; lithium borohydride; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.2: Paterson aldol reaction;
DOI:10.1021/ja071461o

Reference yield:

: 942133-08-6
(2S,4R,5R,E)-5-hydroxy-9-(4-methoxybenzyloxy)-4,7-dimethyl-3-oxonon-6-en-2-yl benzoate

: 942133-23-5
(2S,3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-9-(4-methoxybenzyloxy)-4,7-dimethylnon-6-ene-2,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - -40 °C

2: LiBH₄ / tetrahydrofuran / 76 h / -78 - 20 °C

With 2,6-dimethylpyridine; lithium borohydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja071461o