The title molecule, diisopropyl (diisopropoxyphosphorylmethylsulfonylmethylsulfonylmethyl)phosphonate, C15H34O10P2S2, represents a disulfone of a phosphate ester that has been investigated as a target for chemotherapy. The disulfone has four half‐molecules with crystallographic twofold symmetry in the asymmetric unit. The S=O, P=O and P—O bonds average 1.439, 1.472 and 1.567 Å, respectively. Three isopropyl groups are each disordered over two sites, two of them in a 2:1 ratio and the other in a 3:2 ratio.

A modular replacement approach to the synthesis of sulfonucleotide analogs prepared from condensation of nucleoside aldehydes with bis phosphonate Horner-Wadsworth-Emmons reagents is disclosed. These analogs were shown to be inhibitors of Neisseria meningitidis CSS (NmCSS), which is a key enzyme in the biosynthesis of the capsular polysaccharides required for bacterial infection.

Four neutral vinyl sulfones, two of which are paired with phosphonate groups, are described. The compounds are diisopropyl (2-phenylethenylsulfonylmethyl)phosphonate, C(15)H(23)O(5)PS, (I), diisopropyl {[2-(7-methoxy-1,3-benzodioxol-5-yl)ethenylsulfonyl]methylsulfonylmethyl}phosphonate, C(18)H(27)O(10)PS(2), (II), bis(trans-2-phenylethenyl) sulfone, C(16)H(14)O(2)S, (III), and bis(trans-2-phenylethenylsulfonyl)methane, C(17)H(16)O(4)S(2), (IV). Their structures can be considered as highly functionalized mimics of mono-, di- and triphosphates. These phosphate isosteres are currently of interest as agents for enzyme inhibition in both cancer and HIV therapy. All except one of the compounds has Z' > 1. The lone exception is (IV), a disulfone with twofold crystallographic symmetry. Geometrically, the sulfone functionality is found to be a good mimic for phosphate. The principal effect of the vinyl group is to shorten the S-C(vinyl) distance relative to the S-CH(2) distance by ca 0.05 A. The S-C-S and S-C-P backbones resemble the P-O-P backbone but are not identical because the S-C and P-C distances are longer than the P-O distance and the S-C-S and S-C-P angles are more acute than the P-O-P angle. No prior crystal structures of comparable compounds have been published.

The title compound, diisopropyl (diisopropoxyphosphorylmethylsulfonylmethyl)phosphonate, C14H32O8P2S, is a monosulfone of a diphosphate ester that has been investigated as a target for chemotherapy. The molecule is in a quasi‐gauche conformation with an approximate twofold axis. The S=O, P=O and P—O bonds average 1.444, 1.474 and 1.574 Å, respectively.