(1'R,4R,5S)-(-)-4-[2'-(tert-butyldimethylsilyloxy)-1'-(benzyloxy)-ethyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane

Base Information

Chemical Name:(1'R,4R,5S)-(-)-4-[2'-(tert-butyldimethylsilyloxy)-1'-(benzyloxy)-ethyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane
CAS No.:855269-58-8
Molecular Formula:C₂₂H₃₆O₄Si
Molecular Weight:392.611
Hs Code.:

Synonyms:(1'R,4R,5S)-(-)-4-[2'-(tert-butyldimethylsilyloxy)-1'-(benzyloxy)-ethyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane

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Chemical Property of (1'R,4R,5S)-(-)-4-[2'-(tert-butyldimethylsilyloxy)-1'-(benzyloxy)-ethyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane

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Technology Process of (1'R,4R,5S)-(-)-4-[2'-(tert-butyldimethylsilyloxy)-1'-(benzyloxy)-ethyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane

There total 6 articles about (1'R,4R,5S)-(-)-4-[2'-(tert-butyldimethylsilyloxy)-1'-(benzyloxy)-ethyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane 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: 62.0%

: 100-39-0
benzyl bromide

: 116669-77-3
(1R,4'R,5'S)-(-)-1-(2',2'-dimethyl-5'-vinyl-1',3'-dioxolan-4'-yl)-2-(tert-butyldimethylsilyloxy)-1(R)-ethan-1-ol

: 855269-58-8
(1'R,4R,5S)-(-)-4-[2'-(tert-butyldimethylsilyloxy)-1'-(benzyloxy)-ethyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane

Guidance literature:: (1R,4'R,5'S)-(-)-1-(2',2'-dimethyl-5'-vinyl-1',3'-dioxolan-4'-yl)-2-(tert-butyldimethylsilyloxy)-1(R)-ethan-1-ol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.333333h;

benzyl bromide; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1016/j.tetasy.2005.03.014

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 855269-58-8
(1'R,4R,5S)-(-)-4-[2'-(tert-butyldimethylsilyloxy)-1'-(benzyloxy)-ethyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 89 percent / imidazole / CH₂Cl₂ / 3 h / 20 °C

2.1: potassium tert-butoxide / tetrahydrofuran / 4 h / 20 °C

2.2: 82 percent / tetrahydrofuran / 3 h / -78 - 20 °C

3.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

3.2: 62 percent / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; potassium tert-butylate; sodium hydride; In tetrahydrofuran; dichloromethane; 2.2: Wittig olefination;
DOI:10.1016/j.tetasy.2005.03.014

Reference yield:

: 217309-46-1
5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose

: 855269-58-8
(1'R,4R,5S)-(-)-4-[2'-(tert-butyldimethylsilyloxy)-1'-(benzyloxy)-ethyl]-2,2-dimethyl-5-vinyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium tert-butoxide / tetrahydrofuran / 4 h / 20 °C

1.2: 82 percent / tetrahydrofuran / 3 h / -78 - 20 °C

2.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

2.2: 62 percent / tetrahydrofuran / 2 h / 20 °C

With potassium tert-butylate; sodium hydride; In tetrahydrofuran; 1.2: Wittig olefination;
DOI:10.1016/j.tetasy.2005.03.014