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59490

Sigma-Aldrich

(4R,5R)-2,2-Dimethyl-α,α,α′,α′-tetra(2-naphthyl)dioxolane-4,5-dimethanol

≥99.0% (sum of enantiomers, HPLC)

Synonym(s):

(−)-2,3-O-Isopropylidene-1,1,4,4-tetra(2-naphthyl)-L-threitol, (−)-DINOL

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About This Item

Empirical Formula (Hill Notation):
C47H38O4
CAS Number:
Molecular Weight:
666.80
Beilstein:
6168481
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Assay

≥99.0% (sum of enantiomers, HPLC)

optical activity

[α]20/D −116±2°, c = 1% in ethyl acetate

optical purity

enantiomeric ratio: ≥99.5:0.5 (HPLC)

mp

213-216 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1(C)O[C@H]([C@@H](O1)C(O)(c2ccc3ccccc3c2)c4ccc5ccccc5c4)C(O)(c6ccc7ccccc7c6)c8ccc9ccccc9c8

InChI

1S/C47H38O4/c1-45(2)50-43(46(48,39-23-19-31-11-3-7-15-35(31)27-39)40-24-20-32-12-4-8-16-36(32)28-40)44(51-45)47(49,41-25-21-33-13-5-9-17-37(33)29-41)42-26-22-34-14-6-10-18-38(34)30-42/h3-30,43-44,48-49H,1-2H3/t43-,44-/m1/s1

InChI key

QWADMRIAKWGVBF-NDOUMJCMSA-N

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Articles

Apart from numerous examples using TADDOLs in metal-catalyzed asymmetric reactions, Rawal recently reported that TADDOLs could be used as Brønsted acid organocatalysts in highly stereoselective hetero-Diels–Alder reactions.

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