Uses
4-Nitrobenzyl 2-Diazo-3-(trimethylsilyloxy)-3-butenoate is a useful research chemical compound used in the preparation and synthesis of (±)??-??asparenomycin C.
Synthesis
p-Nitrobenzyl 2-Diazo-3-trimethylsilyloxy-3-butenoate is prepared by silylation of the corresponding diazoacetoacetate with a silyl triflate (Trimethylsilyl Trifluoromethanesulfonate or t-Butyldimethylsilyl Trifluoromethanesulfonate) and Triethylamine in CH2Cl2. For large scale preparations the use of Chlorotrimethylsilane, Potassium Iodide (one equivalent), and Et3N in acetonitrile is more advantageous.
storage
Should be stored in solution in a dry, dark, cold place. The solid form is stable for several months in the refrigerator. The solid reagent is not shock sensitive but exothermic decomposition takes place on melting, generating 200 cal g-1 (138 cal g-1 for the TBDMS ether). Decomposition can also be initiated by metallic impurities (Cu, Rh, etc.).
