(4R,5S)-ethyl-5-(3-(tert-butyldiphenylsilyloxy)propyl)-2,2-di-methyl-1,3-dioxolane-4-carboxylate

Base Information

Chemical Name:(4R,5S)-ethyl-5-(3-(tert-butyldiphenylsilyloxy)propyl)-2,2-di-methyl-1,3-dioxolane-4-carboxylate
CAS No.:1442433-15-9
Molecular Formula:C₂₇H₃₈O₅Si
Molecular Weight:470.681
Hs Code.:

Synonyms:(4R,5S)-ethyl-5-(3-(tert-butyldiphenylsilyloxy)propyl)-2,2-di-methyl-1,3-dioxolane-4-carboxylate

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Chemical Property of (4R,5S)-ethyl-5-(3-(tert-butyldiphenylsilyloxy)propyl)-2,2-di-methyl-1,3-dioxolane-4-carboxylate

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Technology Process of (4R,5S)-ethyl-5-(3-(tert-butyldiphenylsilyloxy)propyl)-2,2-di-methyl-1,3-dioxolane-4-carboxylate

There total 2 articles about (4R,5S)-ethyl-5-(3-(tert-butyldiphenylsilyloxy)propyl)-2,2-di-methyl-1,3-dioxolane-4-carboxylate 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: 92.0%

: 1442433-13-7
(2R,3S)-ethyl-6-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyhexanoate

: 77-76-9
2,2-dimethoxy-propane

: 1442433-15-9
(4R,5S)-ethyl-5-(3-(tert-butyldiphenylsilyloxy)propyl)-2,2-di-methyl-1,3-dioxolane-4-carboxylate

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 0 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tet.2015.06.036

Reference yield:

: 118231-26-8
C₂₄H₃₂O₃Si

: 1442433-15-9
(4R,5S)-ethyl-5-(3-(tert-butyldiphenylsilyloxy)propyl)-2,2-di-methyl-1,3-dioxolane-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: C₄₈H₅₄N₆O₄; potassium carbonate; potassium osmate(VI) dihydrate; C₆FeN₆^(3-)*2K⁽¹⁺⁾; methanesulfonamide / tert-butyl alcohol; water / 24 h / 0 °C

2: camphor-10-sulfonic acid / dichloromethane / 3 h / 20 °C

With potassium osmate(VI) dihydrate; methanesulfonamide; camphor-10-sulfonic acid; C₄₈H₅₄N₆O₄; C₆FeN₆^(3-)*2K⁽¹⁺⁾; potassium carbonate; In dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2013.04.069

Reference yield:

: 1442433-15-9
(4R,5S)-ethyl-5-(3-(tert-butyldiphenylsilyloxy)propyl)-2,2-di-methyl-1,3-dioxolane-4-carboxylate

: 1442433-50-2
(2E,7S,8E,10S,11S)-ethyl 14-hydroxy-11-((4-methoxybenzyl)oxy)-7,10-bis(methoxymethoxy)tetradeca-2,8-dienoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / 0 °C

2.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

3.1: sodium hexamethyldisilazane / tetrahydrofuran / 4 h / -78 - 0 °C

4.1: acetic acid / water / 3 h / 50 °C

5.1: N-ethyl-N,N-diisopropylamine / 2 h / 0 °C

6.1: sodium hydride / tetrahydrofuran / 6 h / 0 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

8.1: dmap; triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C

8.2: 12 h / 0 - 20 °C

9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 36 h / Inert atmosphere; Reflux

10.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 - 0 °C / Inert atmosphere

11.1: benzene / 8 h / 80 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; toluene; benzene;
DOI:10.1016/j.tetlet.2013.04.069