(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid

Base Information

• Chemical Name: (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid
• CAS No.: 105181-72-4
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.335
• Mol file: 105181-72-4.mol

Synonyms:(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid

Chemical Property of (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid

Chemical Property:

• Boiling Point: 499.1±45.0 °C(Predicted)
• Density: 1?+-.0.06 g/cm3(Predicted)

Purity/Quality:

99.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid

There total 31 articles about (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric 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: 85.0%

di-tert-butyl dicarbonate (24424-99-5) + (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid hydrochloride → (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid (105181-72-4)

Guidance literature:

With sodium hydroxide; sodium carbonate; In 1,4-dioxane; at 20 ℃; for 8h;

DOI:10.1248/cpb.51.702

Reference yield: 39.0%

aqueous potassium hydroxide + aqueous sodium hypochlorite + dipercarbonate de O,O-t-butyle (3236-56-4) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) + sodium hydrogensulfite → (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-65-8,76498-21-0,77171-41-6,82848-28-0,105181-72-4,116661-86-0)

Guidance literature:

With potassium hydroxide; cyfluthrin; In hexane; water; ethyl acetate; acetonitrile;

Reference yield: 32.5%

di-tert-butyl dicarbonate (24424-99-5) + 2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid (209173-80-8) → (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-65-8,76498-21-0,77171-41-6,82848-28-0,105181-72-4,116661-86-0) + (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid (105181-72-4)

Guidance literature:

With TEA; In tetrahydrofuran; water;

DOI:10.1016/S0223-5234(00)00187-2

upstream raw materials:

N-(tert-butyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

di-tert-butyl dicarbonate

2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid

(3S)-3-tert-butoxycarbonylamino-1,1-dichloro-4-phenyl-2-butanone

Downstream raw materials:

N-Boc-(2S,3S)-AHPA-L-Leu-tert-butyl ester

((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester

[(1S,2S)-1-Benzyl-3-((R)-4-tert-butylcarbamoyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester

Boc-Apns-Dmt-NHtBu