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

Base Information

• Chemical Name: O-[(2S)-hydroxy-3-nitropropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol
• CAS No.: 118466-98-1
• Molecular Formula: C₁₉H₂₇NO₅
• Molecular Weight: 349.427
• Mol file: 118466-98-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about O-[(2S)-hydroxy-3-nitropropanoyl]-(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: 90.0%

nitromethane (75-52-5) + <1R-(1α,2β,5α)>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl dihydroxyacetate (108794-12-3) → O-[(2S)-hydroxy-3-nitropropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol (118466-98-1)

Guidance literature:

potassium fluoride; In isopropyl alcohol; at 20 ℃;

DOI:10.1016/S0040-4039(00)86707-6

Reference yield:

nitromethane (75-52-5) + (1R,3R,4S)-8-phenylmenthyl glyoxylate (84312-20-9) → O-[(2S)-hydroxy-3-nitropropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol (118466-98-1) + O-[(2R)-hydroxy-3-nitropropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Guidance literature:

With aluminum oxide; In tetrahydrofuran; at 20 ℃; for 24h; Title compound not separated from byproducts;

DOI:10.1016/j.tetlet.2003.09.152

Reference yield: 92.0%

tert-butyldimethylsilyl chloride (18162-48-6) + O-[(2S)-hydroxy-3-nitropropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol (118466-98-1) → O-[(2S)-t-butyldimethylsilyloxy-3-nitropropanoyl]-(1'R,2'S,5'R)-8'-phenylmenthol

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 17h;

DOI:10.1016/j.tet.2004.04.005

upstream raw materials:

nitromethane

<1R-(1α,2β,5α)>-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl dihydroxyacetate

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

Downstream raw materials:

O-[3-amino-(2S)-t-butyldimethylsilyloxypropanoyl]-(1'R,2'S,5'R)-8'phenylmenthol

(S)-3-Amino-2-triethylsilanyloxy-propionic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester