O-[(2S)-hydroxy-(3R)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Base Information

• Chemical Name: O-[(2S)-hydroxy-(3R)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol
• CAS No.: 640279-63-6
• Molecular Formula: C₂₆H₃₃NO₅
• Molecular Weight: 439.552

Synonyms:O-[(2S)-hydroxy-(3R)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Chemical Property of O-[(2S)-hydroxy-(3R)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of O-[(2S)-hydroxy-(3R)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

There total 3 articles about O-[(2S)-hydroxy-(3R)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol 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: 63.0%

2-Phenylnitroethane (6125-24-2) + (1R,3R,4S)-8-phenylmenthyl glyoxylate (84312-20-9) → (2R,3R)-2-Hydroxy-3-nitro-4-phenyl-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester + (2R,3S)-2-Hydroxy-3-nitro-4-phenyl-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester + O-[(2S)-hydroxy-(3R)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol (640279-63-6) + O-[(2S)-hydroxy-(3S)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Guidance literature:

With aluminum oxide; In tetrahydrofuran; at 20 ℃; for 7h;

DOI:10.1016/j.tetlet.2003.09.154

Reference yield:

2-Phenylnitroethane (6125-24-2) + (1R,3R,4S)-8-phenylmenthyl glyoxylate (84312-20-9) → O-[(2S)-hydroxy-(3R)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol (640279-63-6) + O-[(2S)-hydroxy-(3S)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol + O-[2-hydroxy-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Guidance literature:

With aluminum oxide; In tetrahydrofuran; at 20 ℃; for 7h;

DOI:10.1016/j.tet.2004.04.005

Reference yield:

2-Phenylnitroethane (6125-24-2) + (1R,3R,4S)-8-phenylmenthyl glyoxylate (84312-20-9) → O-[(2S)-hydroxy-(3R)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol (640279-63-6) + O-[(2S)-hydroxy-(3S)-3-nitro-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Guidance literature:

With aluminum oxide; at -20 ℃; for 24h;

DOI:10.1021/jo0358269

upstream raw materials:

2-Phenylnitroethane

(1R,3R,4S)-8-phenylmenthyl glyoxylate

Downstream raw materials:

methyl (2S)-2-(((2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl)amino)-4-methylpentanoate

O-[(3R)-tert-butoxycarbonylamino-(2S)-hydroxy-2,3-isopropylidene-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

O-[(3R)-tert-butoxycarbonylamino-(2S)-hydroxy-4-phenylbutanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

[(3R)-tert-butoxycarbonylamino-(2S)-hydroxy-2,3-isopropylidene-4-phenylbutanoyl]-L-leucine methyl ester

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