N-ForMyl-L-isoleucine (1S)-1-[[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]Methyl]dodecyl Ester

Base Information

• Chemical Name: N-ForMyl-L-isoleucine (1S)-1-[[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]Methyl]dodecyl Ester
• CAS No.: 1072902-75-0
• Molecular Formula: C₂₉H₅₃NO₅
• Molecular Weight: 495.744
• Mol file: 1072902-75-0.mol

Synonyms:L-Isoleucine Orlistat;N-ForMyl-L-isoleucine (1S)-1-[[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]Methyl]dodecyl Ester;Orlistat USP Related Compound E

Chemical Property of N-ForMyl-L-isoleucine (1S)-1-[[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]Methyl]dodecyl Ester

Chemical Property:

• PSA: 85.19000
• LogP: 7.72220

Purity/Quality:

99% ^*data from raw suppliers

L-IsoleucineOrlistat ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: L-Isoleucine Orlistat is an impurity of Orlistat (O686500). Also, L-Isoleucine Orlistat is a Tetrahydrolipstatin (THL) analogue as inhibitor of the formation or hydrolysis of the endocannabinoid 2-arachidonoylglycerol (2-AG). L-Isoleucine Orlistat is an impurity of Orlistat (O686500). Also, L-Isoleucine Orlistat is a Tetrahydrolipstatin (THL) analogue as inhibitor of the formation or hydrolysis of the endocannabinoid 2-arachidonoylglycerol (2-AG).

Technology Process of N-ForMyl-L-isoleucine (1S)-1-[[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]Methyl]dodecyl Ester

There total 7 articles about N-ForMyl-L-isoleucine (1S)-1-[[(2S,3S)-3-Hexyl-4-oxo-2-oxetanyl]Methyl]dodecyl Ester 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: 56.0%

L-isoleucine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester (1072902-95-4) + formyl acetic anhydride (2258-42-6) → OMDM-188 (1072902-75-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1021/jm800978m

Reference yield: 7.2%

formic anhydride (1558-67-4) + C28H53NO4 → OMDM-188 (1072902-75-0)

Guidance literature:

In dichloromethane; at -10 - -5 ℃; for 2h;

Reference yield:

N-[(phenylmethoxy)carbonyl]-L-isoleucine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester (1072902-88-5) → OMDM-188 (1072902-75-0)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium on activated charcoal; hydrogen / tetrahydrofuran

2: dichloromethane

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2012.05.101

upstream raw materials:

L-isoleucine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester

formyl acetic anhydride

N-[(phenylmethoxy)carbonyl]-L-isoleucine-(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester

formic anhydride

Refernces

• 1、 Johnston, Meghan,Bhatt, Shachi R.,Sikka, Surina,Mercier, Richard W.,West, Jay M.,Makriyannis, Alexandros,Gatley, S. John,Duclos Jr., Richard I.. "Assay and inhibition of diacylglycerol lipase activity". . p. 4585 - 4592. Retrieved 2012/08/08.