DEAD, diethyl azodicarboxylate

Scheme 3 Abbreviations EDC, 1-[3-(dimethylamino)propyl]-3-ethyl-carbodiimidejhydrochloride HOBt, 1-hydroxybenzotriazole DEAD, diethyl azodicarboxylate.

DIAD = diisopropyl azodicarboxylate. DEAD = diethyl azodicarboxylate. 

Scheme 3. Synthesis of MGd-BSO conjugate. DEAD = diethyl azodicarboxylate Fmoc = 9-fluorenylmethoxycarbonyl.

The acetate ofthis alcohol is used in a Diels-Alder reaction with the interesting dienophile DEAD (diethyl azodicarboxylate—in orange). 

Scheme 5.48. Enzymatic synthesis of 2-amino-3-hydroxy-l, 6-hexanedicarboxylic acids using serine hydroxymethyl transferases (SHMT). DEAD = diethyl azodicarboxylate.

Ac, acetyl AIBN, azobis(isobutanonitrile) All, allyl AR, aryl Bn, benzyl f-BOC, ferf-butoxycarbonyl Bu, Butyl Bz, benzoyl CAN, ceric ammonium nitrate Cbz, benzyloxycarbonyl m-CPBA, m-chloroperoxybenzoic acid DAST, diethylaminosulfur trifluoride DBU, l,8-diazabicyclo[5.4.0]undec-7-ene DCC, /V. /V - d i eye I oh e x y I c ar bo -diimide DCM, dichloromethyl DCMME, dichloromethyl methyl ether DDQ, 2,3-dichloro-5,6-dicyano-l,4-benzoquinone DEAD, diethyl azodicarboxylate l-(+)-DET, L-(+)-diethyl tartrate l-DIPT, L-diisopropyl tartrate d-DIPT, D-diisopropyl tartrate DMAP, 4-dimethylaminopyridine DME, 1,2-dimethoxyethane DMF, /V./V-dimethylformamide DMP, 2,2-dimethoxypropane Et, ethyl Im, imidazole KHMDS, potassium hexamethyldisilazane Me, methyl Me2SO, dimethyl sulfoxide MOM, methoxymethyl MOMC1, methoxymethyl chloride Ms, methylsulfonyl MS, molecular sieves NBS, N-bromosuccinimide NIS, /V-iodosuccinimide NMO, /V-methylmorpho-line N-oxide PCC, pyridinium chlorochromate Ph, phenyl PMB, / -methoxvbenzyl PPTs, pyridiniump-toluenesulfonate i-Pr, isopropyl Py, pyridine rt, room temperature TBAF, tetrabutylammonium fluoride TBS, ferf-butyl dimethylsilyl TBDMSC1, f-butylchlorodimethylsilane Tf, trifhioromethylsulfonyl Tf20, trifluoromethylsulfonic anhydride TFA, trifluoroacetic acid THF, tetrahydrofuran TMS, trimethylsilyl TPAP, tetra-n-propylammonium perruthenate / -TsOH. / -toluenesulfonic acid... 

Treatment of the 1,3-dithiolane 318 with TPP/DEAD/HN3 provided a mixture of 1,4-dithianes 319, 320, and 1,4-dithiin 321 in moderate yields (52-71% TPP = tetraphenylporphyrin DEAD = diethyl azodicarboxylate Equation 32) <1999T801>. 

---