392758

Sigma-Aldrich

AD-mix-α

Synonym(s):
AD-mix-alpha
MDL number:
PubChem Substance ID:

Quality Level

SMILES string

CC[C@@H]1CN2CCC1CC2[C@H](Oc3nnc(O[C@@H](C4CC5CCN4C[C@@H]5CC)c6ccnc7ccc(OC)cc67)c8ccccc38)c9ccnc%10ccc(OC)cc9%10

InChI

1S/C48H54N6O4/c1-5-29-27-53-21-17-31(29)23-43(53)45(35-15-19-49-41-13-11-33(55-3)25-39(35)41)57-47-37-9-7-8-10-38(37)48(52-51-47)58-46(44-24-32-18-22-54(44)28-30(32)6-2)36-16-20-50-42-14-12-34(56-4)26-40(36)42/h7-16,19-20,25-26,29-32,43-46H,5-6,17-18,21-24,27-28H2,1-4H3/t29-,30+,31-,32+,43-,44-,45-,46-/m1/s1

InChI key

YUCBLVFHJWOYDN-PPIALRKJSA-N

Related Categories

General description

Contains chiral ligand (DHQ)2PHAL

Application

Catalyst employed in the Sharpless Asymmetric Dihyroxylation of (E,E)- or (E,Z)-1,3-dienoates. Also used in the preparation of ß-hydroxy-γ-lactones from ß,γ-unsaturated esters.
Reagent for Sharpless Asymmetric Dihydroxylation.
AD-mix-α has been used in the asymmetric dihydroxylation (AD) step of synthesizing (+)-enantiomeric form of a potent anti-inflammatory methyl picolinate alkaloid from methyl 5-bromopicolinate.

Packaging

10, 50, 250 g in glass bottle

Components

Mixture contains:
(DHQ)2PHAL (Cat. No. 392723)0.0016 mole
Potassium carbonate, powder0.4988 mole
Potassium ferricyanide0.4988 mole
Potassium osmate dihydrate0.0007 mole

pictograms

Exclamation markEnvironment

signalword

Warning

hazcat

Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Supp Hazards

EUH032

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 2

Flash Point F

Not applicable

Flash Point C

Not applicable

Certificate of Analysis

Certificate of Origin

Aldrichimica Acta, 27, 70-70 (1994)
Chemical Reviews, 94, 2483-2483 (1994)
European Journal of Organic Chemistry, 2669-2669 (2006)
First asymmetric synthesis of CJ-14877 and its enantiomer and their interleukin-1? inhibitory activities.
Aoyagi Y, et al.
Bioorganic & Medicinal Chemistry Letters, 19(7), 1876-1878 (2009)
The Journal of Organic Chemistry, 57, 2768-2768 (1992)
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