cis-2-Phenyl-1,3-dioxan-5-ol

Chemical Properties

White Solid

Uses

Reactant involved in synthesis of biologically active molecules including:

• Arachidonoylglycerol mimetics selective for CB1 receptors
• Core disaccharides from Streptococcus pneumoniae type 23F capsular polysaccharide antigen
• Anionic demdrimers for use as antibacterial agents

Reactant involved in synthesis of:

• Isoglycerol methacrylate-lactide amphiphilic block copolymers and supramolecular aggregates
• Hyperbranched polyalkenamer-polyesters via acyclic diene metathesis polymerization
• Protected branched glycerol oligomer

Definition

ChEBI: Benzaldehyde glyceryl acetal is a member of dioxanes.

General Description

cis-1,3-O-Benzylideneglycerol participates as a monomer in the preparation of novel oligomeric prepolymers. cis-derivatives are obtained from the acylation and etherification of cis-1,3-O-benzylideneglycerol.

Synthesis

4.2.7 Synthesis of cis-2-phenyl-1,3-dioxan-5-ol (18): In a reaction flask fitted with a Dean-Stark splitter, a solution of freshly distilled benzaldehyde (48 mL, 50 g, 0.47 mol) and glycerol (44 mL, 55 g, 0.60 mol) in toluene (69 mL) was added, followed by dropwise addition of concentrated sulfuric acid (3 drops). The reaction mixture was heated to reflux until the water was completely separated (8.5 mL of water was collected). After completion of the reaction, the mixture was cooled to room temperature and the solvent was removed by distillation under reduced pressure. The white solid obtained was recrystallized by isopropyl ether/petroleum ether solvent mixture. The precipitate was collected and analyzed by fast column chromatography (column size: = 6 cm, h = 15 cm, eluent volume V = 50 mL, cyclohexane/ethyl acetate = 2:1, Rf = 0.16) for further purification to afford the target product 18 as a colorless solid (42.6 g, 0.24 mol, 50% yield). Melting point (Mp) = 81 °C; 1H NMR (DMSO-d6) δ: 3.48-3.52 (m, 1H, OCH2CHOH), 3.91-3.97 (m, 2H, OCH2CHOH), 4.01-4.07 (m, 2H, OCH2CHOH), 4.99 (d, J = 4.8 Hz, 1H, OH), 5.53 (s , 1H, CHPh), 7.33-7.40 (m, 3H, benzene ring 3',4',5'-H), 7.42-7.47 (m, 2H, benzene ring 2',6'-H); 13C NMR (DMSO-d6) δ: 62.4 (OCH2CHOH), 71.4 (2C, OCH2CHOH), 100.2 (CHPh) 126.2 (2C, benzene ring C-2', C-6'), 127.9 (2C, benzene ring C-3', C-5'), 128.5 (benzene ring C-4'), 138.9 (benzene ring C-1'); IR (pure sample, cm-1 ): 3271, 2916, 2851, 1450, 1385, 1339, 1277, 1153, 1084, 995, 976, 806, 741, 694; HRMS (m/z): [M + H]+ calculated value C10H13O3, 181.0859; measured value, 181.0878; HPLC (Method 1): tR = 11.7 min, purity 95.4%.

References

[1] Journal of the American Chemical Society, 1995, vol. 117, # 34, p. 8757 - 8768
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 5, p. 1032 - 1044
[3] Journal of Chemical Research, Miniprint, 1981, # 1, p. 256 - 281
[4] Journal of the American Chemical Society, 2008, vol. 130, # 44, p. 14444 - 14445
[5] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1930, vol. 191, p. 211,220