(2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate

Base Information

• Chemical Name: (2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate
• CAS No.: 143100-05-4
• Molecular Formula: C₃₃H₄₈N₂O₄S
• Molecular Weight: 568.821
• Mol file: 143100-05-4.mol

Synonyms:(2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate

Chemical Property of (2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate

There total 5 articles about (2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate 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: 64.0%

iodomethylbenzene (620-05-3) + (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate (188183-27-9) → (2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate (143100-05-4) + (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate (143100-04-3)

Guidance literature:

With lithium diisopropyl amide; Yields of byproduct given; 1.) THF, -78 deg C, 1 h, 2.) THF, HMPA, -78 deg C to r.t.; r.t., 1 d;

DOI:10.1021/jo00088a034

Reference yield: 52.0%

(2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-phenyl-2-cyanopropanoate (188183-31-5) + methyl iodide (74-88-4) → (2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate (143100-05-4) + (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate (143100-04-3)

Guidance literature:

With lithium diisopropyl amide; Yield given. Title compound not separated from byproducts; 1.) THF, -78 deg C, 1 h, 2.) THF, HMPA, -78 deg C to r.t.; r.t., 1 d;

DOI:10.1021/jo00088a034

Reference yield:

(-)-10-dicyclohexylsulfamoyl-D-isoborneol (96303-88-7) → (2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-methyl-3-phenylpropanoate (143100-05-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / silver cyanide / toluene / 4 h / 80 °C

2: 1.) LDA, 2.) HMPA / 1.) THF, -78 deg C, 1 h, 2.) THF, RT, 1 d

With N,N,N,N,N,N-hexamethylphosphoric triamide; silver cyanide; lithium diisopropyl amide; In toluene;

DOI:10.1016/S0957-4166(00)86182-0

upstream raw materials:

iodomethylbenzene

(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate

(1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl (E)-2-cyanocinnamate

methyl iodide

Downstream raw materials:

(S)-(+)-2-cyano-2-methyl-3-phenylpropanoic acid

(2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-methyl-3-phenylpropanoate

(R)-2-amino-2-methyl-3-phenylpropanoic acid

(2S)-methyl 2-carbamoyl-2-methyl-3-phenylpropanoate