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418951 Sigma-Aldrich

(DHQD)2Pyr

97%

Synonym: Hydroquinidine-2,5-diphenyl-4,6-pyrimidinediyl diether

  • CAS Number 149725-81-5

  • Empirical Formula (Hill Notation) C56H60N6O4

  • Molecular Weight 881.11

  •  MDL number MFCD00198108

  •  PubChem Substance ID 24866252

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Cinchona Alkaloids, Dihydroxylation,
Quality Level   100
assay   97%
optical activity   [α]20/D −390°, c = 1.2 in methanol
mp   247-250 °C (lit.)
SMILES string   CC[C@H]1CN2CCC1CC2[C@@H](Oc3nc(nc(O[C@H](C4CC5CCN4C[C@@H]5CC)c6ccnc7ccc(OC)cc67)c3-c8ccccc8)-c9ccccc9)c%10ccnc%11ccc(OC)cc%10%11
InChI   1S/C56H60N6O4/c1-5-35-33-61-27-23-39(35)29-49(61)52(43-21-25-57-47-19-17-41(63-3)31-45(43)47)65-55-51(37-13-9-7-10-14-37)56(60-54(59-55)38-15-11-8-12-16-38)66-53(50-30-40-24-28-62(50)34-36(40)6-2)44-22-26-58-48-20-18-42(64-4)32-46(44)48/h7-22,25-26,31-32,35-36,39-40,49-50,52-53H,5-6,23-24,27-30,33-34H2,1-4H3/t35-,36-,39-,40-,49+,50+,52-,53-/m0/s1
InChI key   SWKRDCRSJPRVNF-DOGDSVMGSA-N

Description

Application

(DHQD)2Pyr may be used:
• To catalyze the enantioselective allylic amination of alkylidene cyanoacetates with dialkyl azodicarboxylates.
• To prepare 10(R),11-Dihydroxydihydroquinine and 10(S),11-dihydroxydihydroquinine via the Sharpless catalytic asymmetric dihydroxylation.
• In the total synthesis of okadaic acid, a protein phosphatase inhibitor.

Packaging

1 g in glass bottle

Legal Information

Sold under license from Rhodia Pharma Solutions.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
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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