• 6,10-Dibenzyl-N,N'-dimethyl-N,N,N',N'-tetrakis(4-methylbenzyl)-1,4-dioxaspiro[4.5]decane-(2R,3R)-diylbis(methylammonium) Bis(tetrafluoroborate) [=(R,R)-TaDiAS-2nd] (CAS 2010983-27-2) - TCI D3475 - AMI Scientific
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TCI

CAS 2010983-27-2

6,10-Dibenzyl-N,N'-dimethyl-N,N,N',N'-tetrakis(4-methylbenzyl)-1,4-dioxaspiro[4.5]decane-(2R,3R)-diylbis(methylammonium) Bis(tetrafluoroborate) [=(R,R)-TaDiAS-2nd] TCI D3475

6,10-Dibenzyl-N,N'-dimethyl-N,N,N',N'-tetrakis(4-methylbenzyl)-1,4-dioxaspiro[4.5]decane-(2R,3R)-diylbis(methylammonium) Bis(tetrafluoroborate) [=(R,R)-TaDiAS-2nd] TCI D3475
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Rp 3.453.450,00
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TCI D3475, catalogue name 6,10-Dibenzyl-N,N'-dimethyl-N,N,N',N'-tetrakis(4-methylbenzyl)-1,4-dioxaspiro[4.5]decane-(2R,3R)-diylbis(methylammonium) Bis(tetrafluoroborate), also written (R,R)-TaDiAS-2nd, is a second-generation chiral catalyst from the TaDiAS family: a tartaric acid–derived quaternary bis-ammonium salt designed specifically for asymmetric synthesis. Its full name describes a spiroacetal framework carrying two stereocentres of R,R configuration together with two positively charged ammonium centres, each balanced by a tetrafluoroborate anion. Catalysts of this type function as chiral phase-transfer catalysts, shuttling nucleophilic anions from an aqueous phase into an organic phase while simultaneously directing their attack from one face only.

The property that gives this reagent its high value in the laboratory is the presence of two ammonium centres within a single molecule, which creates a tight chiral pocket around the ion pair. Four 4-methylbenzyl groups, together with the two benzyl groups on the spiro skeleton, assemble a firmly defined steric environment, so a substrate can only approach comfortably through one particular orientation and the reaction delivers product with high enantiomeric excess. The tetrafluoroborate counter-anion is weakly coordinating, leaving the ammonium centres available to organise the reacting ion pair rather than being tied up by their own counter-ion.

In Indonesian laboratories this catalyst is typically used in university research groups, graduate methodology projects, and pharmaceutical or fine-chemical development work where a single enantiomer of a target molecule is required. It is normally handled at small scale on the bench, in catalytic loadings, within biphasic reaction systems set up for asymmetric alkylation and related transformations. Because it is supplied as a defined single stereoisomer, it also serves as a dependable reference catalyst when a group is validating or comparing asymmetric methods.

  • Asymmetric phase-transfer alkylation — the bis-ammonium structure carries nucleophilic anions into the organic phase while its chiral pocket forces attack from a single face, giving high enantioselectivity.
  • Enantioselective synthesis of chiral building blocks — the fixed (2R,3R) configuration of the spiroacetal backbone allows researchers to target one predictable enantiomeric series throughout a synthetic route.
  • Pharmaceutical intermediate development — a defined single-stereoisomer catalyst supports work where only one enantiomer of an active molecule is biologically relevant and the other must be suppressed.
  • Asymmetric catalysis methodology research — the second-generation TaDiAS design, with four 4-methylbenzyl and two benzyl groups, makes it a useful probe of how steric bulk controls stereochemical outcome.
  • Reference catalyst for comparative screening — because its structure, stereochemistry and CAS identity are unambiguous, it serves as a benchmark against which newly prepared chiral catalysts can be measured.

Brand TCI
CAS number 2010983-27-2
Molecular formula —
Purity —
Category Chemistry > Asymmetric Synthesis > Chiral Catalysts, Chiral Ligands, Chiral Reagents
Pack sizes available in TCI research-scale catalogue packs; please confirm the required pack size when ordering
Physical form —
Storage keep in the tightly closed original container in a cool, dry place
  • Chemical class: tartaric acid–derived quaternary bis-ammonium salt with bis(tetrafluoroborate) counter-anions
  • Stereochemistry: single defined stereoisomer, (2R,3R) configuration, (R,R)-TaDiAS-2nd

Store the material in its original tightly closed container in a cool, dry place, protected from moisture and away from direct sunlight and sources of heat. As an ionic quaternary ammonium salt, it should be kept from prolonged exposure to humid air; a desiccator or a sealed secondary container is appropriate for opened packs, and weighing is best done quickly with clean dry spatulas to avoid caking. Handle in a fume hood using safety glasses, gloves, and a laboratory coat, and avoid generating or inhaling dust. Keep the container clearly labelled, return it to storage immediately after use, and follow the manufacturer's safety data sheet together with your institution's chemical waste procedures for disposal of residues and contaminated solvents.

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