(4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-en-1-ol

Base Information

Chemical Name:(4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-en-1-ol
CAS No.:1551543-91-9
Molecular Formula:C₂₇H₄₈O₅Si
Molecular Weight:480.761
Hs Code.:

Synonyms:(4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-en-1-ol

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Chemical Property of (4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-en-1-ol

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Technology Process of (4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-en-1-ol

There total 4 articles about (4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-en-1-ol 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: 99.0%

: 1551543-71-5
(4R,5S,6S,7R,E)-methyl 5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-enoate

: 1551543-91-9
(4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-en-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/ol500004k

Reference yield:

: 1551543-85-1
(2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione

: 1551543-91-9
(4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: lithium borohydride / diethyl ether / 0.33 h / -26 - -15 °C

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 7 h / 20 °C

3: dichloromethane / 18 h / 20 °C

4: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 °C

5: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; lithium borohydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In tetrahydrofuran; diethyl ether; dichloromethane; 3: |Wittig Olefination;
DOI:10.1021/ol500004k

Reference yield:

: 1551543-88-4
(2R,3S,4S,5R)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-diol

: 1551543-91-9
(4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 7 h / 20 °C

2: dichloromethane / 18 h / 20 °C

3: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 °C

4: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In tetrahydrofuran; dichloromethane; 2: |Wittig Olefination;
DOI:10.1021/ol500004k