305806-21-7

Basic information

• Product Name: tert-butyl (R)-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate
• Synonyms: tert-butyl (R)-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate
• CAS NO: 305806-21-7
• Molecular Weight: 321.417
• Mol File: 305806-21-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: tert-butyl (R)-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (R)-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate(305806-21-7)
• EPA Substance Registry System: tert-butyl (R)-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoate(305806-21-7)

Safety Data

• Hazardous Substances Data: 305806-21-7(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 74786-02-0 1-(tert-butyldimethylsilyloxy)-1-tert-butoxyethylene 
• 155396-71-7 tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate 
• 861256-22-6 tert-butyl 3-(4-dimethylaminobenzamido)-2-diazo-3-phenylpropanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 265669-72-5 tert-butyl (3R,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate 
• 161671-34-7 tert-butyl (R)-3-amino-3-phenylpropionate 
• 861256-31-7 tert-butyl 3-(4-dimethylaminobenzamido)-3-phenylpropanoate 

Downstream Products

• 158807-47-7 (R)-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropan-1-ol 
• 161671-34-7 tert-butyl (R)-3-amino-3-phenylpropionate 

Relevant articles and documents

Disulfonimide-catalyzed asymmetric synthesis of β3-amino esters directly from N-Boc-amino sulfones

An asymmetric Mannich reaction of silyl ketene acetals with N-Boc-amino sulfones has been developed. A chiral disulfonimide efficiently catalyzes both the in situ generation of the corresponding N-Boc imines and the asymmetric Mannich reaction with excellent yields and enantioselectivities. Kinetic studies confirm a proposed stepwise mechanism.

Oxazinanones as chiral auxiliaries: Synthesis and evaluation in enolate alkylations and aldol reactions

Homochiral β-amino esters (prepared on multigram scale by lithium amide conjugate addition) are readily transformed into oxazinanones. N-Acyl derivatives of oxazinanones undergo stereoselective enolate alkylation reactions, with higher stereoselectivities observed for the enolate alkylation of (R)-N-propanoyl-4-iso-propyl-6,6-dimethyl-oxazinan-2-one than the corresponding Evans oxazolidin-2-one. A C(4)-iso-propyl stereodirecting group within the oxazinanone conveys higher stereoselectivity than the analogous C(4)-phenyl substituent. gem-Dimethyl substitution at C(6) within the oxazinanone framework facilitates exclusive exocyclic cleavage upon hydrolysis to furnish α-substituted carboxylic acid derivatives and the parent oxazinanone in good yield. Asymmetric aldol reactions of a range of aromatic and aliphatic aldehydes with the chlorotitanium enolate of (R)-N-propanoyl-4-iso- propyl-6,6-dimethyl-oxazinan-2-one proceed with excellent diastereoselectivity. Hydrolysis of the aldol products affords homochiral α-methyl-β- hydroxy-carboxylic acids. The Royal Society of Chemistry 2006.