175789-29-4

Basic information

• Product Name: (3S,6S)-6-((S)-2-tert-Butoxycarbonyl-5-oxo-pyrrolidin-1-yl)-3-methyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester
• Synonyms: (3S,6S)-6-((S)-2-tert-Butoxycarbonyl-5-oxo-pyrrolidin-1-yl)-3-methyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester
• CAS NO: 175789-29-4
• Molecular Weight: 416.474
• Mol File: 175789-29-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,6S)-6-((S)-2-tert-Butoxycarbonyl-5-oxo-pyrrolidin-1-yl)-3-methyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,6S)-6-((S)-2-tert-Butoxycarbonyl-5-oxo-pyrrolidin-1-yl)-3-methyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester(175789-29-4)
• EPA Substance Registry System: (3S,6S)-6-((S)-2-tert-Butoxycarbonyl-5-oxo-pyrrolidin-1-yl)-3-methyl-3,6-dihydro-[1,2]oxazine-2-carboxylic acid benzyl ester(175789-29-4)

Safety Data

• Hazardous Substances Data: 175789-29-4(Hazardous Substances Data)

Upstream product

• 3426-71-9 Benzyl N-hydroxycarbamate 

Downstream Products

• 529484-01-3 benzyl (3S)-c-6-[(5'S)-5'-(tert-butyloxycarbonyl)-2'-oxo-pyrrolidin-1'-yl]-t-4,t-5-dihydroxy-r-3-methyl-1,2-oxazinane-2-carboxylate 
• 35418-16-7 L-t-butyl pyroglutamate 

Relevant articles and documents

Chiral N-dienyl-L-pyroglutamic esters in asymmetric hetero-Diels-Alder reactions with acylnitroso dienophiles

Asymmetric Diels-Alder reaction of the N-dienyl-L-pyroglutamic esters 1a-h with acyl nitroso dienophiles 4a-h gave diastereoisomeric adducts 6a-n, 7a-n with 12-90% de, depending on solvents and temperature. An interpretation was given. The 'allylic effect' (π(C=C) - σ*(N-C) MO interactions) was found to be effective to account for the conformations of the adducts.