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

Base Information

Chemical Name:(2S,3S)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid tert-butyl ester
CAS No.:191328-28-6
Molecular Formula:C₂₆H₃₅N₃O₃Si
Molecular Weight:465.668
Hs Code.:

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

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

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

There total 7 articles about (2S,3S)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid tert-butyl ester 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: 94.0%

: 98946-18-0
tert-Butyl 2,2,2-trichloroacetimidate

: 191328-42-4
(2S,3S)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid

: 191328-28-6
(2S,3S)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid tert-butyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane;
DOI:10.1016/S0040-4039(97)00713-2

Reference yield:

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

: 191328-28-6
(2S,3S)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 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: 86 percent / potassium bistrimethylsilyl amide, triisopropylbenzenesulfonyl azide, HOAc / tetrahydrofuran / 0.5 h / -78 °C

5: 97 percent / LiOH, H₂O₂ / tetrahydrofuran; H₂O

6: 94 percent / BF₃OEt₂ / CH₂Cl₂

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

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 191328-28-6
(2S,3S)-2-Azido-3-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 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: 86 percent / potassium bistrimethylsilyl amide, triisopropylbenzenesulfonyl azide, HOAc / tetrahydrofuran / 0.5 h / -78 °C

6: 97 percent / LiOH, H₂O₂ / tetrahydrofuran; H₂O

7: 94 percent / BF₃OEt₂ / CH₂Cl₂

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