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392758

Sigma-Aldrich

AD-mix-α

Synonym(s):

AD-mix-alpha

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10 G
$62.40
50 G
$214.00
250 G
$716.00

About This Item

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

$62.40


In StockDetails


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form

powder

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

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.[1]
Catalyst employed in the Sharpless Asymmetric Dihyroxylation of (E,E)- or (E,Z)-1,3-dienoates.[2] Also used in the preparation of ß-hydroxy-γ-lactones from ß,γ-unsaturated esters.[3]
Reagent for Sharpless Asymmetric Dihydroxylation.[4][5]

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

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable


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Aldrichimica Acta, 27, 70-70 (1994)
The Journal of Organic Chemistry, 57, 2768-2768 (1992)
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)
Chemical Reviews, 94, 2483-2483 (1994)
European Journal of Organic Chemistry, 2669-2669 (2006)

Related Content

The Sharpless Lab pursues useful new reactivity and general methods for selectively controlling chemical reactions.

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    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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