93250-97-6

Basic information

• Product Name: Methyl 4-benzyl-2-tert-butyl-3-formyl-1,3-oxazolidine-4-carboxylate
• Synonyms: Methyl 4-benzyl-2-tert-butyl-3-formyl-1,3-oxazolidine-4-carboxylate
• CAS NO: 93250-97-6
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.37
• Mol File: 93250-97-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl 4-benzyl-2-tert-butyl-3-formyl-1,3-oxazolidine-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-benzyl-2-tert-butyl-3-formyl-1,3-oxazolidine-4-carboxylate(93250-97-6)
• EPA Substance Registry System: Methyl 4-benzyl-2-tert-butyl-3-formyl-1,3-oxazolidine-4-carboxylate(93250-97-6)

Safety Data

• Hazardous Substances Data: 93250-97-6(Hazardous Substances Data)

Upstream product

• 93250-89-6 methyl (2R,4S)-2-(tert-butyl)-1,3-oxazolane-4-carboxylate 
• 190080-34-3 (2RS,5S)-2-(tert-butyl)-5-methoxycarbonyl-1,3-oxazolidine 
• 630-19-3 pivalaldehyde 
• 100-39-0 benzyl bromide 
• 93250-91-0 (2R,4S)-2-tert-butyl-3-formyl-1,3-oxazolidine-4-carboxylic acid methyl ester 

Downstream Products

• 365402-94-4 (S)-(+)-2-amino-2-hydroxymethyl-3-phenylpropionic acid methyl ester 
• 205817-28-3 methyl (S)-2-benzyl-2-(tert-butoxycarbonylamino)-3-hydroxypropanoate 
• 205817-29-4 (S)-2-(Benzyloxyamino-methyl)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 205817-31-8 C₂₀H₂₉N₃O₈ 

Relevant articles and documents

New fast and practical method for the enantioselective synthesis of α-vinyl, α-alkyl quaternary α-amino acids

We describe a fast and practical enantioselective synthesis of (S)-N-Cbz-α-vinyl, phenylalanine, suitable for the preparation of different N-Cbz-α-vinyl aminoacids of both configurations. The new protocol exploits a Wittig reaction on highly enantiomeric enriched N-Cbz-α-formyl-α-alkyl amino esters, readily accessible from (l)-serine through a stereoselective alkylation of Seebach's oxazolidine, carried out with a significant improvement of the previously reported method. The synthetic scheme is suitable for gram scale preparation of the desired product with a 94% ee.

α-ALKYLATION OF SERINE WITH SELF-PRODUKTION OF THE CENTER OF CHIRALITY

The lithium enolate 6 of methyl (2R,4S)-2-t-butyl-3-formyl-oxazolidine-4-carboxylate (4b) derived from (S)-(+)-serine can be generated with LDA in THF solution at -75 deg C.Alkylations (9) and hydroxyalkylations (10,11) occur preferentially (>95:5) from the Re-face of the donor center (relative topicity lk).This stereochemical course is derived from the absolute configuration of 2-deuterio- and 2-methyl-serine (12,13) obtained through the enolate 6.