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Key Documents

COO/COA

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

Name: (4<I>S-trans</I>)-2,2-Dimethyl-<I>α,α,α′,α′</I>-tetra(2-naphthyl)-1,3-dioxolane-4,5-dimethanol
Brand: ALDRICH

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

Certificates of Analysis (COA)

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B. Schmidt et al.

Angewandte Chemie (International Edition in English), 103, 100-100 (1991)

D. Seebach et al.

Angewandte Chemie (International Edition in English), 103, 991-991 (1991)

Angewandte Chemie (International Edition in English), 31, 84-84 (1992)

Articles

TADDOL

The chiral auxiliaries TADDOLs (α,α,α,α-tetraaryl-1,3-dioxolane-4,5- dimethanols) developed by Seebach's group have found numerous applications in asymmetric synthesis ranging from utilization as stoichiometric chiral reagents or in Lewis acid mediated reactions, to roles in catalytic hydrogenation and stereoregular metathesis polymerization.

Chiral Diols

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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