93788-47-7

Basic information

• Product Name: 3-Butenoic acid, 2-diazo-3-[(trimethylsilyl)oxy]-, (4-nitrophenyl)methyl ester
• Synonyms: 4-Nitrobenzyl 2-diazo-3-(trimethylsilyloxy)-3-butenoate;p-Nitrobenzyl 2-diazo-3-(trimethylsilyloxy)-3-butenoate;CH28410 P-NITROBENZYL 2-DIAZO-3-TRIMETHYLSILYLOXY-3-BUTENOATE
• CAS NO: 93788-47-7
• Molecular Formula: C14H17N3O5Si
• Molecular Weight: 335.392
• Mol File: 93788-47-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3-Butenoic acid, 2-diazo-3-[(trimethylsilyl)oxy]-, (4-nitrophenyl)methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Butenoic acid, 2-diazo-3-[(trimethylsilyl)oxy]-, (4-nitrophenyl)methyl ester(93788-47-7)
• EPA Substance Registry System: 3-Butenoic acid, 2-diazo-3-[(trimethylsilyl)oxy]-, (4-nitrophenyl)methyl ester(93788-47-7)

Safety Data

• Hazardous Substances Data: 93788-47-7(Hazardous Substances Data)

Upstream product

• 16029-98-4 trimethylsilyl iodide 
• 82551-63-1 4-nitrobenzyl 2-diazo-3-oxo-butanoate 
• 61312-84-3 4-nitrobenzyl 3-oxobutanoate 
• 619-73-8 4-nitrobenzyl chloride 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 

Downstream Products

• 98269-57-9 3-(1-methylethylidene)-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone 
• 93861-39-3 (3S,4R)-3-[(1R)-(tert-butyldimethyl-silyloxy)ethyl]-4-[3-(4-nitrobenzyloxy)carbonyl-2-oxo-3-diazopropyl]azetidin-2-one 
• 112245-22-4 p-nitrobenzyl 4-{(3R,4R)-3-[(R)-1-fluoroethyl]-2-oxoazetidin-4-yl}-2-diazo-3-oxobutyrate 
• 74288-39-4 (3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one 
• 98391-92-5 3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone 
• 101067-94-1 Benzoic acid (R)-1-{(2R,3S)-2-[3-diazo-3-(4-nitro-benzyloxycarbonyl)-2-oxo-propyl]-4-oxo-azetidin-3-yl}-ethyl ester 
• 98269-71-7 1-(tert-butyldimethylsilyl)-3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone 
• 98269-63-7 3-<(E)-2-bromo-1-methylethylidene>-4-<3-(((p-nitrobenzyl)oxy)carbonyl)-3-diazo-2-oxopropyl>-2-azetidinone 
• 83997-55-1 (3R,4R)-3-ethyl-4-<3-diazo-2-oxo-3-<<(p-nitrobenzyl)oxy>carbonyl>propyl>-2-azetidinone 

Relevant articles and documents

Efficient method for silylation of p-nitrobenzyl-2-diazoacetoacetate

An efficient new method for the silylation of p-nitrobenzyl-2- diazoacetoacetate using hexamethyl disilane and iodine is presented. Copyright Taylor & Francis LLC.

Process for preparing an enol silyl ether compound

A process for preparing an enol silyl ether compound from a diazoacetoacetic acid ester having the general formula (IV): STR1 wherein R1 is a lower alkyl group having 1 to 6 carbon atoms, phenyl group, a substituted phenyl group, an aralkyl group or allyl group, and R2, R3 and R4 are the same or mutually different and each is a lower alkyl group having 1 to 6 carbon atoms, which comprises reacting a diazoacetoacetic acid ester having the general formula (I): STR2 wherein R1 is the same as defined above, with a trialkylsilyl chloride having the general formula (II): STR3 wherein R2, R3 and R4 are the same as defined above, in an inert solvent in the presence of an organic base and an alkali halide having the general formula (III): wherein M is an alkaline metal and X is bromine atom or iodine atom. The desired compound is useful as an intermediate for synthesis of carbapenem β-lactam antibiotics.

Useful Chemistry of 3-(1-Methylethylidene)-4-acetoxy-2-azetidinone: A Formal Synthesis of (+/-)-Asparenomycin C

3-(1-Methylethylidene)-4-acetoxy-2-azetidinone (5) was prepared from the addition of chlorosulfonyl isocyanate to 1-acetoxy-3-methylbuta-1,2-diene.Isolated as a stable crystalline solid, this material is a versatile intermediate and is used in a formal sy