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265004

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

Name: (4R,5R)-2,2-Dimethyl-α,α,α′,α′-tetraphenyldioxolane-4,5-dimethanol
Brand: ALDRICH

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

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About This Item

Empirical Formula (Hill Notation):

C₃₁H₃₀O₄

CAS Number:

93379-48-7

Molecular Weight:

466.57

UNSPSC Code:

12352005

NACRES:

NA.22

PubChem Substance ID:

24856048

MDL number:

MFCD00064467

Beilstein/REAXYS Number:

3657855

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Properties

Quality Segment

100

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

Description

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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