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264997

Sigma-Aldrich

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

97%

Synonym(s):

(+)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-D-threitol, (+)-trans-α,α′-(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol), (4S,5S)-4,5-Bis(diphenylhydroxymethyl)-2,2-dimethyldioxolane

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About This Item

Empirical Formula (Hill Notation):
C31H30O4
CAS Number:
93379-49-8
Molecular Weight:
466.57
Beilstein/REAXYS Number:
4724097
MDL number:
MFCD00010079
UNSPSC Code:
12352005
PubChem Substance ID:
24856047
NACRES:
NA.22

assay

97%

optical activity

[α]19/D +67°, c = 1 in chloroform

mp

193-196 °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-/m0/s1

InChI key

OWVIRVJQDVCGQX-NSOVKSMOSA-N

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Application

Ligand for enantioselective Lewis-acid mediated Diels-Alder,[1] allyltitanation of aldehydes,[2] and Michael-Mukaiyama additions promoted by chiral Ti-complexes.[3]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
1451974V
1451974
1325701
1298358
S30448

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Bernardi, A. et al.
Tetrahedron Letters, 36, 1363-1363 (1995)
Quinkert, G. et al.
Tetrahedron Letters, 33, 3617-3617 (1992)
A. Hafner et al.
Journal of the American Chemical Society, 114, 2321-2321 (1992)

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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