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Safety Information

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

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About This Item

Empirical Formula (Hill Notation):
C47H38O4
CAS Number:
137365-16-3
Molecular Weight:
666.80
MDL number:
MFCD00142323
UNSPSC Code:
12352005
PubChem Substance ID:
24864540
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.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

393762-1G:
393762-VAR:
393762-250MG:
393762-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
BCBB9927V
BCBB9927
015170/1
040543/1
02515TD

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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

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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