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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 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)

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’.

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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.

TADDOL

TADDOL chiral auxiliaries find diverse applications in asymmetric synthesis, catalysis, and polymerization.

TADDOL

TADDOL chiral auxiliaries find diverse applications in asymmetric synthesis, catalysis, and polymerization.

TADDOL

TADDOL chiral auxiliaries find diverse applications in asymmetric synthesis, catalysis, and polymerization.

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