Skip to Content
Merck
All Photos(1)

Documents

393762

Sigma-Aldrich

(4S-trans)-2,2-Dimethyl-α,α,α′,α′-tetra(2-naphthyl)-1,3-dioxolane-4,5-dimethanol

98%

Synonym(s):

(+)-2,3-O-Isopropylidene-1,1,4,4-tetra(2-naphthyl)-D-threitol, (+)-DINOL, (4S,5S)-2,2-Dimethyl-α,α,α′,α′-tetra(2-naphthyl)dioxolane-4,5-dimethanol

Sign Into View Organizational & Contract Pricing


About This Item

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

Assay

98%

optical activity

[α]20/D +116°, c = 1 in ethyl acetate

optical purity

ee: 99% (HPLC)

mp

214-216 °C (lit.)

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-/m0/s1

InChI key

QWADMRIAKWGVBF-CXNSMIOJSA-N

Application

Reagent for the highly enantioselective addition of primary alkyl Grignards to ketones. Chiral auxiliary used for the asymmetric addition of nucleophiles to carbonyls.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

D. Seebach et al.
Angewandte Chemie (International Edition in English), 103, 991-991 (1991)
B. Schmidt et al.
Angewandte Chemie (International Edition in English), 103, 100-100 (1991)
Angewandte Chemie (International Edition in English), 31, 84-84 (1992)

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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service