<(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate

Base Information

• Chemical Name: <(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate
• CAS No.: 104926-26-3
• Molecular Formula: C₂₈H₄₉NO₄S
• Molecular Weight: 495.767
• Mol file: 104926-26-3.mol

Synonyms:<(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate

Chemical Property of <(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate

There total 11 articles about <(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate 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: 84.0%

4-methylvaleroyl chloride (38136-29-7) + (-)-10-dicyclohexylsulfamoyl-D-isoborneol (96303-88-7) → <(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate (104926-26-3)

Guidance literature:

With silver cyanide; In toluene; at 90 ℃; for 5h;

DOI:10.1016/S0040-4020(01)86059-2

Reference yield: 71.0%

N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((Z)-4-methyl-1-trimethylsilanyloxy-pent-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide (104897-91-8) + di-tert-butyl (E)-azodicarboxylate (870-50-8) → <(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate (104926-26-3) + <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> <(2S)-2-(N,N'-di-tert-butoxycarbonyl)>hydrazinopropionate (110449-41-7) + <(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> <(2R)-2-(N,N'-di-tert-butoxycarbonyl)>hydrazinopropionate (119751-27-8)

Guidance literature:

With titanium(IV) isopropylate; titanium tetrachloride; In dichloromethane; at -78 ℃; for 1h; Yields of byproduct given;

DOI:10.1016/S0040-4020(01)86059-2

Reference yield:

<(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl>propionate (96864-31-2) → <(2S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> 4-methylvalerate (104926-26-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / lithium diisopropylamide / tetrahydrofuran / from -78 degC to r.t. over 3 h

2: 81 percent / Ti-(O-i-Pr)4, TiCl₄ / CH₂Cl₂ / 1 h / -78 °C

3: 1.) CF₃COOH; 2.) H₂ / 2.) PtO₂ / 1.) CH₂Cl₂, 0 degC, 5 min then r.t., 3 h; 2.)EtOH, 75 psi, r.t.

4: 94 percent / ethanol / 60 h / Ambient temperature

5: 84 percent / AgCN / toluene / 5 h / 90 °C

With titanium(IV) isopropylate; silver cyanide; hydrogen; titanium tetrachloride; trifluoroacetic acid; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1016/S0040-4020(01)86059-2

upstream raw materials:

4-methylvaleroyl chloride

(-)-10-dicyclohexylsulfamoyl-D-isoborneol

N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((Z)-4-methyl-1-trimethylsilanyloxy-pent-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide

di-tert-butyl (E)-azodicarboxylate

Downstream raw materials:

N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((E)-4-methyl-1-trimethylsilanyloxy-pent-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide

N,N-Dicyclohexyl-C-[(1S,2R,4R)-7,7-dimethyl-2-((Z)-4-methyl-1-trimethylsilanyloxy-pent-1-enyloxy)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide

L-leucine hydrochloride

<(1S,2R)-10-(N,N-dicyclohexylaminosulfonyl)born-2-yl> (2R)-2-amino-4-methylvalerate