(−)-(4R,5R)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane

[93379-48-7] C31H30O4 (MW 466.57) InChI = 1S/C31H30O4/c1-29(2)34-27(30(32,23-15-7-3-8-16-23)24-17-9-4-10-18-24)28(35-29)31(33,25-19-11-5-12-20-25)26-21-13-6-14-22-26/h3-22,27-28,32-33H,1-2H3/t27-,28-/m1/s1 InChIKey = OWVIRVJQDVCGQX-VSGBNLITSA-N (chiral shift reagent; chiral host in inclusion compounds; chiral reagent; chiral ligand for asymmetric catalysis) Alternate Name: TADDOL. Physical Data: mp: 190–192 °C1a; 195–196.5 °C1b; 192–193 °C;1c,e 193.5–195 °C;1d [α]RTd=−68.5 °(c = 1, CH3Cl);1a [α]d = −60.6 °(c = 1, CH3Cl);1b [α]20d = −67 ° (c = 1, CH3Cl);1c [α]20d = −65.1° (c = 1, CH3Cl);1d [α]20d = −64.6°(c = 1, CH3Cl)1e Solubility: soluble in toluene, cyclohexane, dichloromethane and tetrahydrofuran. Form Supplied in: colorless powder. Preparative Method: commercially available, TADDOL can also be obtained from dimethyl or diethyl tartrate (eq 1).1 Purification: recrystallization from pentane,1a MeOH,1b,e or EtOH.1e (1)