(2R,3S)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-(t-butyldimethyl)siloxybutane

Base Information

Chemical Name:(2R,3S)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-(t-butyldimethyl)siloxybutane
CAS No.:139374-05-3
Molecular Formula:C₂₃H₄₀N₂O₅Si
Molecular Weight:452.667
Hs Code.:

Synonyms:(2R,3S)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-(t-butyldimethyl)siloxybutane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3S)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-(t-butyldimethyl)siloxybutane

Chemical Property:

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Technology Process of (2R,3S)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-(t-butyldimethyl)siloxybutane

There total 8 articles about (2R,3S)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-(t-butyldimethyl)siloxybutane 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:

: 2592-18-9
Boc-Thr-OH

: 139374-05-3
(2R,3S)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-(t-butyldimethyl)siloxybutane

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide, 2.) NaBH₄ / 1.) THF, a) 0 deg C, 1 h, b) RT, 5 h, 2.) THF, EtOH, 0 deg C, 30 min

2: 71 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 6 h / Ambient temperature

3: 88 percent / Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

4: 87 percent / NaN₃, 15-crown-5, HMPA / 3 h / 55 °C

5: EtOH / 10percent Pd/C / 2 h / Ambient temperature

6: Et₃N / ethanol / 1 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; 1-hydroxy-pyrrolidine-2,5-dione; sodium azide; 15-crown-5; ethanol; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; dichloromethane;
DOI:10.1246/bcsj.68.1369

Reference yield:

: 139374-02-0
(2R,3R)-2-(t-butoxycarbonyl)amino-1-(t-butyldimethyl)siloxy-3-butanol

: 139374-05-3
(2R,3S)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-(t-butyldimethyl)siloxybutane

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

2: 87 percent / NaN₃, 15-crown-5, HMPA / 3 h / 55 °C

3: EtOH / 10percent Pd/C / 2 h / Ambient temperature

4: Et₃N / ethanol / 1 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; 15-crown-5; ethanol; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane;
DOI:10.1246/bcsj.68.1369

Reference yield:

: 139374-03-1
(2R,3R)-2-(t-butoxycarbonyl)amino-1-(t-butyldimethyl)siloxy-3-(methylsulfonyloxy)butane

: 139374-05-3
(2R,3S)-3-(benzyloxycarbonyl)amino-2-(t-butoxycarbonyl)amino-1-(t-butyldimethyl)siloxybutane

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / NaN₃, 15-crown-5, HMPA / 3 h / 55 °C

2: EtOH / 10percent Pd/C / 2 h / Ambient temperature

3: Et₃N / ethanol / 1 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; 15-crown-5; ethanol; triethylamine; palladium on activated charcoal; In ethanol;
DOI:10.1246/bcsj.68.1369