Synthesis and Crystal Structure of O-Galactopyranosyl N,N-Bis(2-chloroethyl)phosphordiamidate

Chem. J. Chinese Universities ›› 1993, Vol. 14 ›› Issue (10): 1394.

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Synthesis and Crystal Structure of O-Galactopyranosyl N,N-Bis(2-chloroethyl)phosphordiamidate

CHEN Ru-Yu¹, CHEN Xiao-Ru¹, WANG Ru-Ji², WANG Hong-Gen²

1. Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, 300071;
2. Central Laboratory, Nankai University, Tianjin, 300071

Received:1993-01-07 Revised:1993-05-31 Online:1993-10-24 Published:1993-10-24

Abstract

Abstract: To study the antitumor activity of galactopyranosyl phosphoramidate, the title compound was synthesized by phosphorus oxychloride as phosphorylating agent.Apure isomer of the title compound was obtained by recrystallization from a mixture of chloroform and n-hexane, and its single crystal was cultured.The molecular structure of the title compound was determined by X-ray diffraction method.The crystal is monoclinic with space group P2₁, a=1.3474(5) nm, 6=1.0624(4) nm, c=1.6916(5) nm, β=110.55(3)°, V=2.2674 nm³, Mr=463.29, Z=4, D_x=1.35 g/cm³, μ=3.9 cm^-1, F(000)=972.Atotal of 4379 independent reflections were collected, in which 2159 were observed.The final R=0.079 and Rw=0.088.The results of structure analysis indicate that the configuration of the chiral phosphorus atom of the title compound is assigned as R-form.

Key words: Galactopyranosyl, Phosphordiamidate, Crystal structure

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CHEN Ru-Yu, CHEN Xiao-Ru, WANG Ru-Ji, WANG Hong-Gen. Synthesis and Crystal Structure of O-Galactopyranosyl N,N-Bis(2-chloroethyl)phosphordiamidate[J]. Chem. J. Chinese Universities, 1993, 14(10): 1394.

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Synthesis and Crystal Structure of O-Galactopyranosyl N,N-Bis(2-chloroethyl)phosphordiamidate

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