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265004

Sigma-Aldrich

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

97%

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Synonym(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
Empirical Formula (Hill Notation):
C31H30O4
CAS Number:
93379-48-7
Molecular Weight:
466.57
Beilstein/REAXYS Number:
3657855
MDL number:
MFCD00064467
UNSPSC Code:
12352005
PubChem Substance ID:
24856048
NACRES:
NA.22

assay

97%

optical activity

[α]19/D −62.6°, c = 1 in chloroform

mp

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

InChI key

OWVIRVJQDVCGQX-VSGBNLITSA-N

Related Categories

Application

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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
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

Articles

TADDOL

TADDOL chiral auxiliaries find diverse applications in asymmetric synthesis, catalysis, and polymerization.

Chiral Diols

TADDOLs demonstrate versatility in metal-catalyzed asymmetric reactions and as Brønsted acid organocatalysts in hetero-Diels–Alder reactions.

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