(2R,3R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid

Base Information

• Chemical Name: (2R,3R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid
• CAS No.: 156174-45-7
• Molecular Formula: C₁₇H₂₄N₂O₆
• Molecular Weight: 352.387
• Mol file: 156174-45-7.mol

Synonyms:(2R,3R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid

Chemical Property of (2R,3R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid

There total 11 articles about (2R,3R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric 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: 65.0%

((1R,2R)-2-tert-Butoxycarbonylamino-3-hydroxy-1-methyl-propyl)-carbamic acid benzyl ester (168034-29-5) → (2R,3R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid (156174-45-7)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; for 1h;

DOI:10.1246/bcsj.68.1369

Reference yield:

(Z)-N-[(2R)-2-(tert-butoxycarbonylamino)-3-(tertbutyldiphenylsilyloxy)-propylidene]benzylamine N-oxide (158723-49-0,188965-46-0) → (2R,3R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid (156174-45-7)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrahydrofuran / 2 h / -50 °C

2: H₂ / Pd(OH)2-C / methanol / 72 h / 3620.04 Torr / Ambient temperature

3: aq. NaHCO₃ / dioxane / 0.33 h / 0 °C

4: 77 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

5: NaIO₄, RuCl₃ / acetonitrile; CCl₄; H₂O / 0.08 h

With ruthenium trichloride; sodium periodate; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; palladium hydroxide - carbon; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; water; acetonitrile;

DOI:10.1016/S0957-4166(98)00004-4

Reference yield:

[(1R,2R)-2-(Benzyl-hydroxy-amino)-1-(tert-butyl-diphenyl-silanyloxymethyl)-propyl]-carbamic acid tert-butyl ester (188965-48-2) → (2R,3R)-3-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-butyric acid (156174-45-7)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd(OH)2-C / methanol / 72 h / 3620.04 Torr / Ambient temperature

2: aq. NaHCO₃ / dioxane / 0.33 h / 0 °C

3: 77 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: NaIO₄, RuCl₃ / acetonitrile; CCl₄; H₂O / 0.08 h

With ruthenium trichloride; sodium periodate; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; palladium hydroxide - carbon; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; water; acetonitrile;

DOI:10.1016/S0957-4166(98)00004-4

upstream raw materials:

((1R,2R)-2-tert-Butoxycarbonylamino-3-hydroxy-1-methyl-propyl)-carbamic acid benzyl ester

benzyl chloroformate

[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-formyl-ethyl]-carbamic acid tert-butyl ester

(Z)-N-[(2R)-2-(tert-butoxycarbonylamino)-3-(tertbutyldiphenylsilyloxy)-propylidene]benzylamine N-oxide