601501-27-3

Upstream product

• 601501-21-7 (1S,4R,7S)-7-tert-butyl-1-(hydroxymethyl)-6-metoxy-7-methyl-8-oxa-5-azaspiro[3.5]non-5-en-9-one 
• 601501-20-6 (1R,4R,7S)-7-tert-butyl-1-(hydroxymethyl)-6-metoxy-7-methyl-8-oxa-5-azaspiro[3.5]non-5-en-9-one 
• 601501-16-0 (1S,4S,7R)-7-tert-butyl-1-(hydroxymethyl)-6-metoxy-7-methyl-8-oxa-5-azaspiro[3.5]non-5-en-9-one 
• 601501-17-1 (1R,4S,7R)-7-tert-butyl-1-(hydroxymethyl)-6-metoxy-7-methyl-8-oxa-5-azaspiro[3.5]non-5-en-9-one 

Relevant academic research and scientific papers

Synthesis of the four stereoisomers of 1-amino-2-(hydroxymethyl)-cyclobutanecarboxylic acid and their biological evaluation as ligands for the glycine binding site of the NMDA receptor

A synthesis of all four stereoisomers [{1S,2S)-, {1R,2R)-, (1S,2R)-, (1R,2S)-] of 1-amino-2-(hydroxymethyl)cyclobutanecarboxyclic acid is presented. The synthesis is based on the chiral glycine equivalent 1, employed in both enantiomeric forms. The key step involves the cyclization of the silyl-protected iodohydrins 5a-d to the corresponding spiro derivatives 6a-d with the aid of the phosphazenic base tBu-P4. The final compounds were found to display moderate potency as ligands for the glycine binding site of the NMDA receptor. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).