Tetrahedron letters

Synthesis of the (α, α-difluoroalkyl) phosphonate analogue of phosphoserine

DB Berkowitz, Q Shen, JH Maeng

Index: Berkowitz, David B.; Shen, Quanrong; Maeng, Jun-Ho Tetrahedron Letters, 1994 , vol. 35, # 35 p. 6445 - 6448

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Citation Number: 69

Abstract

Abstract The synthesis of the (α, α-difluoroalkyl) phosphonate analogue of L-phosphoserine, 5, in a form appropriate for solid phase peptide synthesis, is reported. Two independent routes are described, starting from L-serine or (R)-isopropylideneglycerol. In each case, PCF 2 C bond formation is achieved by triflate displacement with diethyl lithiodifluoromethylphosphonate.