850796-29-1

Basic information

• Product Name: Sulfoxonium, dimethyl-, (3S)-4-methyl-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]pentylide
• CAS NO: 850796-29-1
• Molecular Formula: C16H23NO4S
• Molecular Weight: 325.429
• Mol File: 850796-29-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Sulfoxonium, dimethyl-, (3S)-4-methyl-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]pentylide(CAS DataBase Reference)
• NIST Chemistry Reference: Sulfoxonium, dimethyl-, (3S)-4-methyl-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]pentylide(850796-29-1)
• EPA Substance Registry System: Sulfoxonium, dimethyl-, (3S)-4-methyl-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]pentylide(850796-29-1)

Safety Data

• Hazardous Substances Data: 850796-29-1(Hazardous Substances Data)

Upstream product

• 24210-19-3 methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate 
• 5034-06-0 trimethyl sulfoxonium chloride 

Downstream Products

• 1253782-95-4 C₂₀H₂₄N₂O₃ 
• 1253782-98-7 C₂₁H₂₅NO₄ 
• 90105-41-2 (S)-1-chloro-3-(benzyloxycarbonylamino)-4-methyl-2-pentanone 

Relevant articles and documents

One-Carbon Chain Extension of Esters to α-Chloroketones: A Safer Route without Diazomethane

The reaction of a variety of methyl esters with dimethylsulfoxonium methylide at 0-25 °C affords the chain-extended β-keto dimethylsulfoxonium ylides. Subsequent treatment with hydrogen chloride in THF proceeds with loss of DMSO to afford the corresponding α-chloroketones. This sequence has been utilized to convert the methyl esters of CBZ-protected alanine and valine to the anti N-protected α-amino epoxides, which are important pharmaceutical intermediates. When the same protocol is applied to BOC-protected phenylalanine methyl ester, epimerization occurs so that the use of a more reactive aryl ester is required. This chemistry provides a practical route to α-chloroketones that avoids the use of toxic and explosive diazomethane.