(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate

Base Information

• Chemical Name: (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate
• CAS No.: 154520-17-9
• Molecular Formula: C₃₁H₅₀N₂O₄S
• Molecular Weight: 546.815
• Mol file: 154520-17-9.mol

Synonyms:(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate

Chemical Property of (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate

There total 4 articles about (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate 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: 66.0%

allyl bromide (106-95-6) + (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-methyl-2-cyanobutanoate (188183-29-1) → (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate (154520-17-9)

Guidance literature:

With potassium carbonate; In acetone; for 24h; Ambient temperature;

DOI:10.1016/S0957-4166(96)00516-2

Reference yield: 63.0%

allyl bromide (106-95-6) + (2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-methyl-2-cyanobutanoate (188183-29-1) → (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate (154520-17-9) + (2S)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate

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:

2-Cyano-3-methylbutanoic acid (22426-27-3) → (2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-cyano-2-isopropyl-4-pentenoate (154520-17-9)

Guidance literature:

Multi-step reaction with 3 steps

1: PCl₅

2: 89 percent / AgCN / toluene / 4 h / 80 °C

3: 63 percent / LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, HMPA, -78 deg C to r.t.; r.t., 1 d

With silver cyanide; phosphorus pentachloride; lithium diisopropyl amide; In toluene;

DOI:10.1021/jo00088a034

upstream raw materials:

allyl bromide

(2RS)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 3-methyl-2-cyanobutanoate

2-Cyano-3-methylbutanoic acid

2-Cyano-3-methylbutanoyl chloride

Downstream raw materials:

(2R)-(1S,2R,4R)-10-(Dicyclohexylsulfamoyl)isobornyl 2-(aminomethyl)-2-isopropylpentanoate

(3R)-3-Isopropyl-3-propyl-2-azetidinone