265004
(4R,5R)-2,2-Dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanol
97%
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
About This Item
Recommended Products
Quality Level
assay
97%
optical activity
[α]19/D −62.6°, c = 1 in chloroform
mp
193-195 °C (lit.)
functional group
ether
hydroxyl
ketal
phenyl
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
Application
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
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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Articles
TADDOL chiral auxiliaries find diverse applications in asymmetric synthesis, catalysis, and polymerization.
TADDOLs demonstrate versatility in metal-catalyzed asymmetric reactions and as Brønsted acid organocatalysts in hetero-Diels–Alder reactions.
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