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265004

Sigma-Aldrich

(4R,5R)-2,2-Dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanol

97%

Sinônimo(s):

(−)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-L-threitol, (−)-trans-α,α′-(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol), (4R,5R)-4,5-Bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane, 1,1,4,4-Tetraphenyl-2,3-O-isopropylidene-L-threitol, TADDOL

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About This Item

Fórmula empírica (Notação de Hill):
C31H30O4
Número CAS:
93379-48-7
Peso molecular:
466.57
Beilstein:
3657855
Número MDL:
MFCD00064467
Código UNSPSC:
12352005
ID de substância PubChem:
24856048
NACRES:
NA.22

Ensaio

97%

atividade óptica

[α]19/D −62.6°, c = 1 in chloroform

pf

193-195 °C (lit.)

grupo funcional

ether
hydroxyl
ketal
phenyl

cadeia de caracteres SMILES

CC1(C)O[C@H]([C@@H](O1)C(O)(c2ccccc2)c3ccccc3)C(O)(c4ccccc4)c5ccccc5

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

chave InChI

OWVIRVJQDVCGQX-VSGBNLITSA-N

Aplicação

Hydrogen-bonding organocatalyst examined in terms of acidity, deprotonation enthalpies and hydrogen bonding

Catalyst involved in synthesis of cyclopropylamines via addition reactions of Grignard reagents to amides

Reactant or reagent involved in:
  • Enantioswitching of catalytic asymmetric hydroboration
  • Synthesis of derivative ligands for asymmetric hydroformylation of alkenes
  • Amide-directed catalytic asymmetric hydroboration of trisubstituted alkenes
  • Addition of deactivated alkyl Grignard reagents to aldehydes

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

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Certificados de análise (COA)

Lot/Batch Number
MKCN1585
MKCJ4223
MKCF8818
MKBR1239V

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Sigma-Aldrich

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Jung-Shen B Tai et al.
Physical review. E, 101(4-1), 042702-042702 (2020-05-20)
Chiral condensed matter systems, such as liquid crystals and magnets, exhibit a host of spatially localized topological structures that emerge from the medium's tendency to twist and its competition with confinement and field coupling effects. We show that the strength
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Artigos

TADDOL

The chiral auxiliaries TADDOLs (α,α,α,α-tetraaryl-1,3-dioxolane-4,5- dimethanols) developed by Seebach's group have found numerous applications in asymmetric synthesis ranging from utilization as stoichiometric chiral reagents or in Lewis acid mediated reactions, to roles in catalytic hydrogenation and stereoregular metathesis polymerization.

Chiral Diols

Apart from numerous examples using TADDOLs in metal-catalyzed asymmetric reactions, Rawal recently reported that TADDOLs could be used as Brønsted acid organocatalysts in highly stereoselective hetero-Diels–Alder reactions.

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