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392758

Sigma-Aldrich

AD-mix-α

Synonym(s):

AD-mix-alpha

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About This Item

MDL number:
MFCD00191975
UNSPSC Code:
12352005
PubChem Substance ID:
329755835
NACRES:
NA.22

form

powder

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

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.

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
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H315,H319,H335,H411

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH032

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

392758-10G:4548173939605
392758-250G:4548173922577
392758-50G:4548173939612
392758-BULK:
392758-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
0000359761
0000359761
0000264420
0000213187
SHBP7982

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Aldrichimica Acta, 27, 70-70 (1994)
The Journal of Organic Chemistry, 57, 2768-2768 (1992)
Chemical Reviews, 94, 2483-2483 (1994)
European Journal of Organic Chemistry, 2669-2669 (2006)
Md Moinuddin Ahmed et al.
The Journal of organic chemistry, 71(20), 7741-7746 (2006-09-26)
The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting
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