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265004

Sigma-Aldrich

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

97%

Synonym(e):

(−)-2,3-O-Isopropyliden-1,1,4,4-tetraphenyl-L-threitol, (−)-trans-α,α′-(2,2-Dimethyl-1,3-dioxolan-4,5-diyl)-bis(diphenylmethanol), (4R,5R)-4,5-Bis-(diphenylhydroxymethyl)-2,2-dimethyldioxolan, 1,1,4,4-Tetraphenyl-2,3-O-isopropyliden-L-threitol, TADDOL

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About This Item

Empirische Formel (Hill-System):
C31H30O4
CAS-Nummer:
93379-48-7
Molekulargewicht:
466.57
Beilstein:
3657855
MDL-Nummer:
MFCD00064467
UNSPSC-Code:
12352005
PubChem Substanz-ID:
24856048
NACRES:
NA.22

Assay

97%

Optische Aktivität

[α]19/D −62.6°, c = 1 in chloroform

mp (Schmelzpunkt)

193-195 °C (lit.)

SMILES String

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

InChIKey

OWVIRVJQDVCGQX-VSGBNLITSA-N

Anwendung

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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meso-1,2-Diphenylethylendiamin 98%

Sigma-Aldrich

458511

meso-1,2-Diphenylethylendiamin

(+)-Diethyl L-tartrat ≥99%

Sigma-Aldrich

156841

(+)-Diethyl L-tartrat

P,P-Dichlorphenylphosphin 97%

Sigma-Aldrich

D71984

P,P-Dichlorphenylphosphin

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
Jung-Shen B Tai et al.
Science (New York, N.Y.), 365(6460), 1449-1453 (2019-10-12)
Starting with Gauss and Kelvin, knots in fields were postulated to behave like particles, but experimentally they were found only as transient features or required complex boundary conditions to exist and could not self-assemble into three-dimensional crystals. We introduce energetically

Artikel

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

Chiral Diols

Unser Team von Wissenschaftlern verfügt über Erfahrung in allen Forschungsbereichen einschließlich Life Science, Materialwissenschaften, chemischer Synthese, Chromatographie, Analytik und vielen mehr..

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