(2S,3S)-2-[((S)-2-Azido-2-methyl-3-triethylsilanyloxy-propionyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

Base Information

Chemical Name:(2S,3S)-2-[((S)-2-Azido-2-methyl-3-triethylsilanyloxy-propionyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester
CAS No.:866555-14-8
Molecular Formula:C₃₄H₅₄N₄O₅Si₂
Molecular Weight:654.998
Hs Code.:

(2S,3S)-2-[((S)-2-Azido-2-methyl-3-triethylsilanyloxy-propionyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

Synonyms:(2S,3S)-2-[((S)-2-Azido-2-methyl-3-triethylsilanyloxy-propionyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

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Chemical Property of (2S,3S)-2-[((S)-2-Azido-2-methyl-3-triethylsilanyloxy-propionyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

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Technology Process of (2S,3S)-2-[((S)-2-Azido-2-methyl-3-triethylsilanyloxy-propionyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

There total 13 articles about (2S,3S)-2-[((S)-2-Azido-2-methyl-3-triethylsilanyloxy-propionyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl 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: 83.0%

: 866555-13-7
(2S,3S)-2-((S)-2-Azido-2-methyl-3-triethylsilanyloxy-propionylamino)-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

: 333-27-7
methyl trifluoromethanesulfonate

: 866555-14-8
(2S,3S)-2-[((S)-2-Azido-2-methyl-3-triethylsilanyloxy-propionyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1002/anie.200500702

Reference yield:

: 866555-26-2
(2R,3R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-oxirane-2-carboxylic acid

: 866555-14-8
(2S,3S)-2-[((S)-2-Azido-2-methyl-3-triethylsilanyloxy-propionyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: hexane / 40 h / 20 °C

2: K₂CO₃ / acetone / 18 h / 20 °C

3: pyridine / CH₂Cl₂ / 0.42 h / 0 °C

4: NaN₃ / dimethylformamide / 0.67 h / 20 °C

5: H₂ / Pd/C / methanol / 1 h / 20 °C / 760 Torr

6: 1.46 g / 1-hydroxy-7-azabenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; iPr₂NEt / CH₂Cl₂ / 18 h / 20 °C

7: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

8: 83 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; sodium azide; 1-hydroxy-7-aza-benzotriazole; hydrogen; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja060064v

Reference yield:

: 866555-11-5
(2S,3S)-2-Azido-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

: 866555-14-8
(2S,3S)-2-[((S)-2-Azido-2-methyl-3-triethylsilanyloxy-propionyl)-methyl-amino]-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: H₂ / Pd/C / methanol / 1 h / 20 °C / 760 Torr

2: 1.46 g / 1-hydroxy-7-azabenzotriazole; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; iPr₂NEt / CH₂Cl₂ / 18 h / 20 °C

3: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

4: 83 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C

With 2,6-dimethylpyridine; 1-hydroxy-7-aza-benzotriazole; hydrogen; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja060064v