160848-03-3

Basic information

• Product Name: methyl (2R,S)-2-(N-benzylamino)-3-(tert-butyldimethylsiloxy)propanoate
• Synonyms: methyl (2R,S)-2-(N-benzylamino)-3-(tert-butyldimethylsiloxy)propanoate
• CAS NO: 160848-03-3
• Molecular Weight: 323.508
• Mol File: 160848-03-3.mol

Chemical Properties

• CAS DataBase Reference: methyl (2R,S)-2-(N-benzylamino)-3-(tert-butyldimethylsiloxy)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2R,S)-2-(N-benzylamino)-3-(tert-butyldimethylsiloxy)propanoate(160848-03-3)
• EPA Substance Registry System: methyl (2R,S)-2-(N-benzylamino)-3-(tert-butyldimethylsiloxy)propanoate(160848-03-3)

Safety Data

• Hazardous Substances Data: 160848-03-3(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 144001-42-3 methyl 2-(benzylamino)-3-hydroxypropanoate 

Downstream Products

• 160848-06-6 methyl (2R,S)-2-(N-benzyl-2-chloro-2-phenylethanamido)-3-(tert-butyldimethylsiloxy)propanoate 
• 160848-07-7 methyl 2-(N-benzyl-2-chloroethanamido)propenoate 
• 263404-03-1 methyl (E)-2-(N-benzylcinnamamido)-3-chloropropanoate 
• 283602-71-1 methyl 2-(N-benzyl-2,2-dichloroethanamido)-3-trichloroacetoxypropanoate 
• 283602-70-0 methyl 2-(N-benzyl-2,2-dichloroethanamido)-3-hydroxy propanoate 
• 160848-10-2 methyl 2-(N-benzyl-2,2-dichloroethanamido)propenoate 
• 867280-03-3 2-(benzylamino)-3-{[tert-butyl(dimethyl)silyl]oxy}-1-propanol 
• 283602-69-7 methyl 2-(N-benzyldichloroethanamido)-3-(tert-butyldimethylsiloxy)propanoate 
• 178100-19-1 methyl (2R,S)-2-(N-benzyl-2-bromoethanamido)-3-(tert-butyldimethylsiloxy)propanoate 
• 160848-05-5 methyl (2R,S)-2-(N-benzyl-2-chloropropanamido)-3-(tert-butyldimethylsiloxy)propanoate 
• 160848-04-4 2-[Benzyl-(2-chloro-acetyl)-amino]-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester 

Relevant articles and documents

New Route to Pyroglutamates via α-Chloro Amide Radical Cyclisation

The tributyltin hydride mediated radical cyclisation of N-(α-chloroacetamido)dehydroalanine derivatives prepared from serine proceeds regioselectively to give pyroglutamates in 47-74percent yield-the cyclisation of the intermediate carbamoylmethyl radical proceeds in a 'disfavoured' 5-endo-trig-manner.

Novel approach to the (-)-sparteine-mediated synthesis of kainoids: Total synthesis of (-)-α-kainic acid by (-)-sparteine-mediated deprotonation

We report a new synthesis of kainoids via allyllithium compounds using an intramolecular cycloalkylation as the key step. Preparation of different substituted pyrrolidines was carried out by using carbamates, that react with the chiral base n-BuLi/(-)-sparteine with strong selection between the diastereotopic protons adjacent to the carbamate group in favour for the pro-S proton. (-)-α-Kainic acid was synthetized from D-serine methyl ester hydrochloride, based on a (-)-sparteine-mediated asymmetric deprotonation of an intermediate carbamate that, by stereospecific anti-SN′S E′ intramolecular cycloalkylation, leads to the pyrrolidine ring precursor of (-)-α-kainic acid, in high yield and diastereoselectivity. Related approaches, starting from L-glutamic acid failed. The intermediate pyrrolidine was further transformed to (-)-α-kainic in three steps. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

A radical cyclisation approach to pyroglutamates

Treatment of serine-derived N-(α-haloacetamido)dehydroalanine derivatives with tributyltin hydride in boiling benzene or toluene afforded pyroglutamates in 47-84% yield. The radical cyclisation reaction, which proceeded regioselectively in a disfavoured 5