Kuyl-Yeheskiely E, Tromp C M, Schaeffer A H, van der Marel G A, van Boom J H
Nucleic Acids Res. 1987 Feb 25;15(4):1807-18. doi: 10.1093/nar/15.4.1807.
The monofunctional phosphitylating reagents bis-(N,N-diethylamino)chlorophosphine and salicylchlorophosphine have been applied for the preparation of H-phosphonates of the amino acids serine, threonine and tyrosine. Experimental evidence showed that the latter reagent was less effective for the synthesis of a tyrosine H-phosphonate. The amino acids (peptide) H-phosphonates of serine or threonine proved to be suitable starting compounds for the formation of a phosphate diester bond with the 5'-OH of a d-nucleoside derivative using pivaloyl chloride as the activating reagent.