(2E)-2-{(4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}ethanol

Base Information

Chemical Name:(2E)-2-{(4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}ethanol
CAS No.:1373934-46-3
Molecular Formula:C₂₅H₃₄O₄Si
Molecular Weight:426.628
Hs Code.:

Synonyms:(2E)-2-{(4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}ethanol

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Chemical Property of (2E)-2-{(4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}ethanol

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Technology Process of (2E)-2-{(4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}ethanol

There total 5 articles about (2E)-2-{(4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}ethanol 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: 91.0%

: 1373934-43-0
ethyl (2E)-2-{(4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}acetate

: 1373934-46-3
(2E)-2-{(4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}ethanol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 0.5h; Inert atmosphere;
DOI:10.1016/j.carres.2012.02.019

Reference yield:

: 1373934-33-8
(4R,5R)-5-(benzyloxy)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxane

: 1373934-46-3
(2E)-2-{(4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}ethanol

Guidance literature:: Multi-step reaction with 5 steps

1: palladium 10% on activated carbon; hydrogen / ethanol / 1 h

2: 1H-imidazole / dichloromethane / 0.6 h / 20 °C / Inert atmosphere

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / Inert atmosphere; Reflux

4: toluene / 2 h / Inert atmosphere; Reflux

5: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere

With 1H-imidazole; palladium 10% on activated carbon; hydrogen; diisobutylaluminium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethanol; dichloromethane; toluene; acetonitrile;
DOI:10.1016/j.carres.2012.02.019

Reference yield:

: 1373934-37-2
(4R,5R)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ol

: 1373934-46-3
(2E)-2-{(4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}ethanol

Guidance literature:: Multi-step reaction with 3 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / Inert atmosphere; Reflux

2: toluene / 2 h / Inert atmosphere; Reflux

3: diisobutylaluminium hydride / dichloromethane; toluene / 0.5 h / -78 °C / Inert atmosphere

With diisobutylaluminium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; toluene; acetonitrile;
DOI:10.1016/j.carres.2012.02.019