The synthesis of phosphonic acid and phosphate analogues of glycerol-3-phosphate and related metabolites

Bioorganic Chemistry

“…For example, the S-enantiomer of 3,4-dihydroxybutyl-l-phosphonic acid (DHBP) has been synthesized as the isosteric analogue of sn-glycerol 3-phosphate (4). The former material is bacteriostatic at low concentrations to certain strain of E. coli and B. subtilus.…”

Organocatalysis in Natural Product Synthesis: A Simple One‐Pot Approach to Optically Active β‐Diols

“…After completion of the reaction (as monitored by TLC), the reaction mixture was filtered through a layer of Celite and evaporated under reduced pressure to obtain the product 13; yield: 14.7 mg (97%). [21] …”

Polycations. II. Chiral ammonium dendrimer synthesis

“…Initial protection of the vicinal diol portion of 1 by acetonide formation followed by substitution of the remaining hydroxyl group by chloride using known procedures [3,4], after purification by column chromatography, yielded the de-…”

“…The material 3 thus isolated (29.43 g, 65.8% total yield) exhibited spectra and elemental analyses in accord with the proposed structure. (4). A solution of 3 (1.52 g, 5.49 mmol) in acetonitrile (15 mL) was placed in a reaction flask fitted with a magnetic stirrer, reflux condenser, and drying tube, and to it was added an excess (2.5 g, 17.6 mmol) of iodomethane.…”

“…2,2-Dimethyl-4-(2Ј-chloroethyl)1,3-dioxolane (2) was prepared as previously reported [4]. All NMR spectra were measured using a Brü ker 400 MHz DPX400 instrument, all optical rotations were measured using a Jasco DIP-140 instrument (1 dm cell, aqueous solution with a sodium vapor lamp), and all CD spectra were measured using a Jasco 500C CD/ORD instru- …”