Description

(S,S)-Taddol (CAS 93379-49-8) is a highly versatile chiral auxiliary and ligand widely used in asymmetric synthesis. With the molecular formula C₃₁H₃₀O₄, this compound features a rigid dioxolane backbone flanked by two diphenylhydroxymethyl groups, providing exceptional stereocontrol in catalytic reactions. Its (4S,5S) configuration ensures high enantioselectivity, making it indispensable for researchers in organic chemistry, pharmaceuticals, and materials science. This product is supplied as a white to off-white crystalline powder with ≥97% purity, ensuring reproducibility in complex transformations such as enantioselective additions, Diels-Alder reactions, and hydrogenations. Store under inert conditions to maintain stability.

Properties

• CAS Number: 93379-49-8
• Complexity: 573
• IUPAC Name: [(4S,5S)-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-/m0/s1
• InChI Key: OWVIRVJQDVCGQX-NSOVKSMOSA-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: 93379-49-8, (S,s)-taddol, (+)-Taddol, ((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol), (+)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane, [(4S,5S)-5-[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-diphenylmethanol, (+)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-D-threitol, (+)-45-Bis[hydroxy(diphenyl)methyl]-22-dimethyl-13-dioxolane, C31H30O4, MFCD00010079, [(4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(diphenylmethanol), (S)-Taddol, (4S,5S)-Taddol, SCHEMBL4383952, DTXSID701317964, (4S,5S)-4,5-Bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane, AKOS016842871, CS-W013767, AS-11054, B2048, T71474, A1-24353, ((4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis-(diphenylmethanol), (2S,3S)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-1,2,3,4-butanetetrol, (4S,5S)-4,5-Bis(hydroxydiphenylmethyl)-2,2-dimethyl-1,3-dioxolane, (+)-trans-Alpha,alpha’-(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol), (4S,5S)-2,2-Dimethyl-alpha,alpha,alpha’,alpha’-tetraphenyldioxolane-4,5-dimethanol, 97%, (4S,5S)-2,2-Dimethyl- alpha , alpha , alpha ‘, alpha ‘-tetraphenyldioxolane-4,5-dimethanol

(S,S)-Taddol is a privileged chiral ligand for asymmetric catalysis, particularly in titanium- and aluminum-mediated reactions. It enables high enantioselectivity in nucleophilic additions to aldehydes and ketones. Researchers also employ it in enantioselective alkylations and cycloadditions. Its rigid structure enhances stereochemical outcomes in synthetic pathways.

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