(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol

Base Information

Chemical Name:(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol
CAS No.:1551543-36-2
Molecular Formula:C₃₁H₅₄O₅Si
Molecular Weight:534.852
Hs Code.:

Synonyms:(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol

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Chemical Property of (3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol

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Technology Process of (3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol

There total 6 articles about (3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-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: 51.0%

: 1551543-94-2
(4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-2,4,6-trimethylnon-2-enal

: 1551544-01-4
(3R,4R,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol

: 1551543-36-2
(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol

Guidance literature:: With (R,R)-trans-EZ-crotyl mix; In dichloromethane; at 20 ℃; for 40h;
DOI:10.1021/ol500004k

Reference yield:

: 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

: 1551543-36-2
(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol

Guidance literature:: Multi-step reaction with 3 steps

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

2: Dess-Martin periodane / dichloromethane / 0 °C

3: (R,R)-trans-EZ-crotyl mix / dichloromethane / 40 h / 20 °C

With lithium aluminium tetrahydride; (R,R)-trans-EZ-crotyl mix; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
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

: 1551543-36-2
(3S,4S,7R,8S,9R,10R,E)-8-((tert-butyldimethylsilyl)oxy)-10-methoxy-12-((4-methoxybenzyl)oxy)-3,5,7,9-tetramethyldodeca-1,5-dien-4-ol

Guidance literature:: Multi-step reaction with 7 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

6: Dess-Martin periodane / dichloromethane / 0 °C

7: (R,R)-trans-EZ-crotyl mix / dichloromethane / 40 h / 20 °C

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