(2S,3R)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid

Base Information

Chemical Name:(2S,3R)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid
CAS No.:191328-43-5
Molecular Formula:C₂₂H₂₇N₃O₃Si
Molecular Weight:409.56
Hs Code.:

Synonyms:(2S,3R)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid

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Chemical Property of (2S,3R)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid

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Technology Process of (2S,3R)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid

There total 6 articles about (2S,3R)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid 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: 88.0%

: 191328-36-6
(S)-3-[(2S,3R)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoyl]-4-benzyl-oxazolidin-2-one

: 191328-43-5
(2S,3R)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid

Guidance literature:: With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water;
DOI:10.1016/S0040-4039(97)00713-2

Reference yield:

: 92808-78-1
(E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol

: 191328-43-5
(2S,3R)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / (CH₃)3CCO₂H / o-xylene / 3 h / 140 °C

2: 78 percent / NaOH / methanol; tetrahydrofuran / 18 h / Ambient temperature

3: 1.) pivaloyl chloride, Et₃N / 1.) THF; 2.) from -78 degC to room t.

4: 80 percent / potassium bistrimethylsilyl amide, triisopropylbenzenesulfonyl azide, HOAc / tetrahydrofuran / 0.5 h / -78 °C

5: 88 percent / LiOH, H₂O₂ / tetrahydrofuran; H₂O

With lithium hydroxide; sodium hydroxide; triisopropylbenzenesulfonyl azide; dihydrogen peroxide; pivaloyl chloride; potassium hexamethylsilazane; acetic acid; triethylamine; Trimethylacetic acid; In tetrahydrofuran; methanol; o-xylene; water;
DOI:10.1016/S0040-4039(97)00713-2

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 191328-43-5
(2S,3R)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: n-BuLi / tetrahydrofuran / 0 °C

2: 90 percent / (CH₃)3CCO₂H / o-xylene / 3 h / 140 °C

3: 78 percent / NaOH / methanol; tetrahydrofuran / 18 h / Ambient temperature

4: 1.) pivaloyl chloride, Et₃N / 1.) THF; 2.) from -78 degC to room t.

5: 80 percent / potassium bistrimethylsilyl amide, triisopropylbenzenesulfonyl azide, HOAc / tetrahydrofuran / 0.5 h / -78 °C

6: 88 percent / LiOH, H₂O₂ / tetrahydrofuran; H₂O

With lithium hydroxide; sodium hydroxide; n-butyllithium; triisopropylbenzenesulfonyl azide; dihydrogen peroxide; pivaloyl chloride; potassium hexamethylsilazane; acetic acid; triethylamine; Trimethylacetic acid; In tetrahydrofuran; methanol; o-xylene; water;
DOI:10.1016/S0040-4039(97)00713-2