105318-43-2

Basic information

• Product Name: p-nitrobenzyl (4R,5R,6S)-6-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-diphenylphosphoryloxy-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate
• CAS NO: 105318-43-2
• Molecular Weight: 708.777
• Mol File: 105318-43-2.mol

Chemical Properties

• CAS DataBase Reference: p-nitrobenzyl (4R,5R,6S)-6-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-diphenylphosphoryloxy-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: p-nitrobenzyl (4R,5R,6S)-6-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-diphenylphosphoryloxy-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate(105318-43-2)
• EPA Substance Registry System: p-nitrobenzyl (4R,5R,6S)-6-<(1R)-1-tert-butyldimethylsilyloxyethyl>-3-diphenylphosphoryloxy-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate(105318-43-2)

Safety Data

• Hazardous Substances Data: 105318-43-2(Hazardous Substances Data)

Upstream product

• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 397887-06-8 5-{(R)-2-[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-nitro-benzyloxycarbonylmethyl)-4-oxo-azetidin-2-yl]-propionyl}-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester 
• 105318-30-7 (3S,4S)-3-<(1R)-1-hydroxyethyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 105318-23-8 (3S,4S)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-phenylthiocarbonylethyl]-1-carboxymethylazetidin-2-one 
• 96035-98-2 (3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone 
• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 619-73-8 4-nitrobenzyl chloride 
• 16869-24-2 4-nitrobenzyl bromoacetate 
• 105318-31-8 (3S,4S)-3-<(1R)-1-tert-butyldimethylsilyloxythyl>-1-(p-nitrobenzyloxycarbonylmethyl)-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 105318-04-5 (3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxy>-2-azetidinone 
• 105318-06-7 (3S,4S)-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R)-1-phenylthiocarbonylethyl>-2-azetidinone 
• 397886-97-4 5-((R)-2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionyl)-4-oxo-3-phenyl-1-oxa-5-aza-spiro[5.5]undec-2-ene-2-carboxylic acid methyl ester 
• 105318-05-6 (3S,4S)-1-(tert-butoxycarbonylmethyl)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R)-1-carboxyethyl>-2-azetidinone 

Relevant articles and documents

2,3-Dihydro-4H-1,3-oxazin-4-ones, novel auxiliaries for the stereoselective synthesis of 1β-methylcarbapenems

Dihydrooxazinones 9, prepared from benzylcyanide in two steps serve as efficient auxiliaries for the stereoselective synthesis of β-methylcarbapenem intermediate 2. Reformatsky-type reactions of 4-acetoxyazetidinone with α-bromopropionyl dihydrooxazinone 10 provided β-methylazetidinones 4 in high diastereoselectivities. The auxiliaries 9 were also easily removed in the Dieckmann cyclization leading to β-methylcarbapenem skeletons. Practical synthesis of β-methylenolphosphates 2 from 4-acetoxyazetidinone 3 was achieved in three steps (61-77% overall yield).

Synthetic studies of carbapenem and penem antibiotics. V. Efficient synthesis of the 1β-methylcarbapenem skeleton

An efficient synthesis of 1β-methylcarbapenem from the 1-(2- oxoazetidinyl)acetate 8 was developed by application of the Dieckmann reaction. Dieckmann-type cyclization of 8 and conversion to the enolphosphate 10 were achieved without epimerization to the 1α-methyl isomer in a one-pot procedure. Treatment with the mercaptan 22 after the phosphorylation resulted in a practical one-pot preparation of the 1β-methylcarbapenem derivative 23 from 8.