2-(S)-azido-2-[3-(tert-butyldimethylsilanyloxy)phenyl]-1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)ethanone

Base Information

• Chemical Name: 2-(S)-azido-2-[3-(tert-butyldimethylsilanyloxy)phenyl]-1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)ethanone
• CAS No.: 899799-13-4
• Molecular Formula: C₂₅H₃₄N₄O₄SSi
• Molecular Weight: 514.721

Synonyms:2-(S)-azido-2-[3-(tert-butyldimethylsilanyloxy)phenyl]-1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)ethanone

Chemical Property of 2-(S)-azido-2-[3-(tert-butyldimethylsilanyloxy)phenyl]-1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)ethanone

Chemical Property:

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Technology Process of 2-(S)-azido-2-[3-(tert-butyldimethylsilanyloxy)phenyl]-1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)ethanone

There total 6 articles about 2-(S)-azido-2-[3-(tert-butyldimethylsilanyloxy)phenyl]-1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)ethanone 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:

C40H58N4O6S2Si → 2-(S)-azido-2-[3-(tert-butyldimethylsilanyloxy)phenyl]-1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)ethanone (899799-13-4)

Guidance literature:

With sodium acetate; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetasy.2006.03.031

Reference yield:

(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)acetic acid (114774-44-6) → 2-(S)-azido-2-[3-(tert-butyldimethylsilanyloxy)phenyl]-1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)ethanone (899799-13-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / tetrahydrofuran / 2 h / -20 °C

2.1: lithium chloride / tetrahydrofuran / -20 - 20 °C

2.2: 10.7 g / triethylamine / tetrahydrofuran / 12 h

3.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C

3.2: glacial acetic acid / tetrahydrofuran / -78 °C

4.1: 2.08 g / sodium acetate / tetrahydrofuran / 20 °C

With sodium acetate; sodium hexamethyldisilazane; triethylamine; lithium chloride; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2006.03.031

Reference yield:

C19H30O4Si → 2-(S)-azido-2-[3-(tert-butyldimethylsilanyloxy)phenyl]-1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ6-benzo[d]isothiazol-2-yl)ethanone (899799-13-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium chloride / tetrahydrofuran / -20 - 20 °C

1.2: 10.7 g / triethylamine / tetrahydrofuran / 12 h

2.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / -78 °C

2.2: glacial acetic acid / tetrahydrofuran / -78 °C

3.1: 2.08 g / sodium acetate / tetrahydrofuran / 20 °C

With sodium acetate; sodium hexamethyldisilazane; lithium chloride; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2006.03.031

upstream raw materials:

(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)acetic acid

2-[3-(tert-butyldimethylsilanyloxy)phenyl]-1-(3-(S)-tert-butyl-1,1-dioxo-1,3-dihydro-1λ⁶-benzo[d]isothiazol-2-yl)-ethanone

m-hydroxyphenylacetic acid

tert-butyldimethylsilyl chloride

Downstream raw materials:

(S)-3-hydroxyphenylglycine

(S)-azido-[3-(tert-butyldimethylsilanyloxy)phenyl]-acetic acid

2-(S)-amino-2-[3-(tert-butyldimethylsilanyloxy)phenyl]ethanol

2-(R)-amino-2-[3-(tert-butyldimethylsilanyloxy)phenyl]ethanol

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