Description

((4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol), commonly known as (-)-TADDOL, is a highly versatile chiral diol with a molecular formula of C₃₁H₃₀O₄ (CAS: 93379-48-7). This optically active compound is widely recognized for its robust stereoselective properties, making it an indispensable reagent in asymmetric synthesis, catalysis, and chiral resolution. The rigid dioxolane backbone and four phenyl groups enhance its ability to form stable complexes with metals and other substrates, facilitating enantioselective transformations. Available in high purity (96-99% ee), this product is ideal for researchers and scientists working in organic chemistry, pharmaceuticals, and material science. Its exceptional stability and predictable reactivity ensure consistent performance in demanding synthetic applications.

Properties

• CAS Number: 93379-48-7
• Complexity: 573
• IUPAC Name: [(4R,5R)-5-[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-diphenyl-methanol
• InChI: 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
• InChI Key: OWVIRVJQDVCGQX-VSGBNLITSA-N
• Exact Mass: 466.21440943
• Molecular Formula: C31H30O4
• Molecular Weight: 466.6
• SMILES: CC1(O[C@H]([C@@H](O1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O)C(C4=CC=CC=C4)(C5=CC=CC=C5)O)C
• Topological: 58.9
• Monoisotopic Mass: 466.21440943
• Synonyms: 93379-48-7, (-)-TADDOL, ((4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol), (4R,5R)-2,2-Dimethyl-alpha,alpha,alpha’,alpha’-tetraphenyldioxolane-4,5-dimethanol, (-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane, [(4R,5R)-5-[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-diphenylmethanol, 2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-L-THREITOL, MFCD00064467, C31H30O4, (-)-trans-Alpha,alpha’-(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol), [(4R,5R)-5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]diphenylmethanol, [(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl]bis(diphenylmethanol), (-)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-L-threitol, (R,R)-TADDOL, SCHEMBL2504692, DTXSID30369334, 96% 99%ee, AC1010, AKOS015895700, CS-W009636, MI11457, NCGC00090592-02, AC-27904, B1614, ST50306945, A1-24352, (2R,3R)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-1,2,3,4-butanetetrol, [5-(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]diphenylmethanol, (4R,5R)-2,2-Dimethyl-alpha,alpha,alpha’,alpha’-tetraphenyldioxolane-4,5-dimethanol, 97%, [(4R,5R)-5-(hydroxydiphenylmethyl)-2,2-dimethyl(1,3-dioxolan-4-yl)]diphenylmet han-1-ol, (4R,5R)-2,2-Dimethyl- alpha , alpha , alpha ‘, alpha ‘-tetraphenyldioxolane-4,5-dimethanol, (4R5R)-2,2,-Dimethyl-a,a,a’,a’-tetraphenyldioxolane-4,5-dimethanol;(-)-Taddol;(-)-trans-a,a-(Dimethyl-1,3-dioxalane-4,5-diyl)bis(dip henylmethanol)

(-)-TADDOL is extensively used as a chiral auxiliary and ligand in asymmetric catalysis, particularly in titanium-mediated reactions such as the Sharpless epoxidation. It serves as a resolving agent for racemic mixtures and is employed in the synthesis of enantiomerically pure compounds. Additionally, its ability to form host-guest complexes makes it valuable in molecular recognition studies and supramolecular chemistry.

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