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(+)-Taddol

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(+)-Taddol Basic information

Product Name:
(+)-Taddol
Synonyms:
  • (+)-4,5-BIS[HYDROXY(DIPHENYL)METHYL]-2,2-DIMETHYL-1,3-DIOXOLANE
  • (4S,5S)-2,2-DIMETHYL-ALPHA,ALPHA,ALPHA',ALPHA'-TETRAPHENYLDIOXOLANE-4,5-DIMETHANOL
  • (4S,5S)-4,5-BIS(DIPHENYLHYDROXYMETHYL)-2,2-DIMETHYL-DIOXOLANE
  • (+)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-D-THREITOL
  • (2S,3S)-(+)-1,1,4,4-TETRAPHENYL-2,3-(2-PROPYLIDENEDIOXY)-BUTANE-1,4-DIOL
  • (2S,3S)-2,3-O-ISOPROPYLIDENE-1,1,4,4-TETRAPHENYL-1,2,3,4-BUTANETETROL
  • (2S,3S)-(+)-4,5-BIS(DIPHENYLHYDROXYMETHYL)-2,2-DIMETHYL-1,3-DIOXOLANE
  • (+)-TADDOL
CAS:
93379-49-8
MF:
C31H30O4
MW:
466.57
Product Categories:
  • chiral
  • Asymmetric Synthesis
  • Dioxanes & Dioxolanes
  • Dioxolanes
  • Synthetic Organic Chemistry
  • TADDOL Series
  • Chiral Oxygen
Mol File:
93379-49-8.mol
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(+)-Taddol Chemical Properties

Melting point:
193-196 °C(lit.)
alpha 
-62.6 º (c=1 in chloroform)
Boiling point:
633.2±50.0 °C(Predicted)
Density 
1.200±0.06 g/cm3(Predicted)
storage temp. 
Inert atmosphere,Room Temperature
form 
powder to crystal
pka
12.28±0.29(Predicted)
color 
White to Almost white
optical activity
[α]19/D +67°, c = 1 in chloroform
BRN 
4724097
InChIKey
RNSJHECWLNVNFE-LOYHVIPDSA-N
CAS DataBase Reference
93379-49-8(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/21/22-36/37/38
Safety Statements 
26-36
WGK Germany 
3
HS Code 
29329990

MSDS

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(+)-Taddol Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

Ligand for enantioselective Lewis-acid mediated Diels-Alder, allyltitanation of aldehydes, and Michael-Mukaiyama additions promoted by chiral Ti-complexes.

Preparation

Preparative Methods of (4R,5R)-2,2-Dimethyl-4,5-bis(hydroxydiphenylmethyl)-1,3-dioxolane: chiral titanates are usually prepared by mixing dichlorodiisopropoxytitanium and a chiral 1,4-diol in toluene. Other solvents such as ether and dichloromethane can also be employed. The alcohol exchange reaction takes place immediately at rt. Wherever necessary, liberated isopropyl alcohol is removed by azeotropic removal with toluene. The chiral 1,4-diols are prepared from dimethyl (or diethyl) tartrate by a two-step procedure comprising acetalization followed by the addition of an aryl Grignard reagent.

storage

Chiral titanates are usually prepared just before use under argon atmosphere. Care should be taken to avoid moisture, especially when a catalytic amount of the reagent is used.

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