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395242

Sigma-Aldrich

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

99%

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About This Item

Empirical Formula (Hill Notation):
C47H38O4
CAS Number:
171086-52-5
Molecular Weight:
666.80
UNSPSC Code:
12352005
PubChem Substance ID:
24864650
NACRES:
NA.22

assay

99%

form

solid

optical activity

[α]20/D +280°, c = 1 in ethyl acetate

mp

200 °C (dec.) (lit.)

SMILES string

CC1(C)O[C@@H]([C@H](O1)C(O)(c2cccc3ccccc23)c4cccc5ccccc45)C(O)(c6cccc7ccccc67)c8cccc9ccccc89

InChI

1S/C47H38O4/c1-45(2)50-43(46(48,39-27-11-19-31-15-3-7-23-35(31)39)40-28-12-20-32-16-4-8-24-36(32)40)44(51-45)47(49,41-29-13-21-33-17-5-9-25-37(33)41)42-30-14-22-34-18-6-10-26-38(34)42/h3-30,43-44,48-49H,1-2H3/t43-,44-/m0/s1

InChI key

WTZVNZRNIOJACO-CXNSMIOJSA-N

Application

(4S-trans)-2,2-Dimethyl-α,α,α′,α′-tetra(1-naphthyl)-1,3-dioxolane-4,5-dimethanol, also known as TADDOL, is a chiral auxiliary that can be used:
  • For the highly enantioselective addition of primary alkyl Grignards to ketones.
  • As an organocatalyst for the activation of carbonyl functionality in vinylogous addition reaction of an aldehyde.
  • As a chiral dopant in the preparation of cholesteric liquid crystal (CLC) having an aggregation-induced-emission dye.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Lasing properties of a cholesteric liquid crystal containing aggregation-induced-emission material
Wang N, et al.
Optics Express, 23(26), 33938-33946 (2015)
Enantiomerically Pure Tertiary Alcohols by TADDOL-Assisted Additions to Ketones or How to Make a Grignard Reagent Enantioselective
Weber B and Seebach D
Angewandte Chemie (International Edition in English), 31(1), 84-86 (1992)
[(2,2-Dimethyl-4-Methylene-4H-1,3-Dioxin-6-yl)Oxy]Trimethylsilane
Villano R, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2008)
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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