(2S,3S)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane

Base Information

• Chemical Name: (2S,3S)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane
• CAS No.: 174302-74-0
• Molecular Formula: C₁₅H₂₂N₂O₅
• Molecular Weight: 310.35

Synonyms:(2S,3S)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane

Chemical Property of (2S,3S)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane

Chemical Property:

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Technology Process of (2S,3S)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane

There total 5 articles about (2S,3S)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane 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: 94.0%

nitromethane (75-52-5) + Boc-L-phenylalaninal (72155-45-4) → (2S,3S)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane (174302-74-0)

Guidance literature:

nitromethane; With (2S,5R)-5-isopropyl-5-methyl-2-(pyridin-2-yl)imidazolidine-4-one; copper diacetate; In ethanol; at 20 ℃; for 1h;

Boc-L-phenylalaninal; In ethanol; at 18 ℃; for 96h; diastereoselective reaction; Catalytic behavior;

DOI:10.1055/s-0033-1338803

Reference yield: 12.3%

(S)-3-tert-butoxycarbonylamino-1-nitro-4-phenyl-2-butanone (174302-72-8) → (2S,3R)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane (161282-72-0) + (2S,3S)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane (174302-74-0)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 1h;

DOI:10.1080/00397919808005092

Reference yield:

nitromethane (75-52-5) + Boc-L-phenylalaninal (72155-45-4) → C15H22N2O5 (181777-01-5) + (2S,3S)-N-tert-butyloxycarbonyl-2-amino-3-hydroxy-1-phenyl-4-nitrobutane (174302-74-0)

Guidance literature:

With pyridine; C₄₃H₃₆N₂O₂S; copper(l) chloride; In ethanol; at 20 ℃; for 22h; optical yield given as %de; diastereoselective reaction;

DOI:10.1039/c0cc03022h

upstream raw materials:

nitromethane

Boc-L-phenylalaninal

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

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

((1S,2S)-3-Amino-1-benzyl-2-hydroxy-propyl)-carbamic acid tert-butyl ester

(2S,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1-(isobutylamino)-4-phenylbutan-2-ol

4-amino-N-((2S,3S)-2-hydroxy-4-phenyl-3-amino-butyl)-N-isobutyl-benzenesulfonamide

C₃₃H₄₃N₃O₃

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