tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate

Base Information

• Chemical Name: tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate
• CAS No.: 203064-74-8
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362
• Mol file: 203064-74-8.mol

Synonyms:tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate

Chemical Property of tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate

There total 3 articles about tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate 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: 67.0%

O-benzyl carbamate (621-84-1) + tert-butyl (E)-crotonate (79218-15-8) → (2R,3R)-tert-butyl 2-hydroxy-3-(N-benzyloxycarbonyl)-aminobutanoate + tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate (203064-74-8) + tert-butyl (2S,3R)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate (203064-64-6) + (2S,3S)-tert-butyl 2-hydroxy-3-(N-benzyloxycarbonyl)-aminobutanoate

Guidance literature:

With sodium hydroxide; potassium osmate(VI); tert-butylhypochlorite; 1,4-bis(9-O-dihydroquinidine)phthalazine; In propan-1-ol; water; for 5h;

DOI:10.1016/j.tet.2006.08.014

Reference yield:

tert-butylhypochlorite (507-40-4) + O-benzyl carbamate (621-84-1) + tert-butyl crotonate (3246-27-3) → tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate (203064-74-8)

Guidance literature:

tert-butylhypochlorite; O-benzyl carbamate; With sodium hydroxide; In water; acetonitrile; at 15 ℃; for 0.5h;

tert-butyl crotonate; With potassium osmate; hydroquinidein 1,4-phthalazinediyl diether; In water; acetonitrile; at 20 ℃; for 1.5h; stereoselective reaction;

DOI:10.1002/chem.202003387

Reference yield:

O-benzyl carbamate (621-84-1) + tert-butyl (E)-crotonate (79218-15-8) → 2-Benzyloxycarbonylamino-3-hydroxy-butyric acid tert-butyl ester + tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate (203064-74-8) + tert-butyl (2S,3R)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate (203064-64-6)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo9720391

upstream raw materials:

O-benzyl carbamate

tert-butyl (E)-crotonate

tert-butylhypochlorite

tert-butyl crotonate

Downstream raw materials:

(1R,2S)-2-(N-Benzyloxycarbonyl-N-methyl)amino-1-(tert-butoxycarbonyl)propyl-1-methanesulfonate

tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxybutanoate

(2S,3S)-tert-Butyl 2-p-nitrobenzoyloxy-3-(N-benzyloxycarbonyl)aminobutanoate

tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)butanoate