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392758 Sigma-Aldrich

AD-mix-α

Synonym: AD-mix-alpha

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Properties

Related Categories Asymmetric Synthesis, Chemical Reagents, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Cinchona Alkaloids,
Quality Level   200
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

Description

General description

Contains chiral ligand (DHQ)2PHAL

Application

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.

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.

Packaging

10, 50, 250 g in glass bottle

Components

Mixture contains:
(DHQ)2PHAL (Cat. No. 392723) 0.0016 mole
Potassium carbonate, powder 0.4988 mole
Potassium ferricyanide 0.4988 mole
Potassium osmate dihydrate 0.0007 mole

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Supplemental Hazard Statements 
EUH032
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Barry Sharpless Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Barry Sharpless Group – Professor Product Portal
Keywords: Asymmetric synthesis, Building blocks, Chemical reactions, Click chemistry, Oxidations, Solvents, transformation

Peer-Reviewed Papers
15

References

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