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418951

Sigma-Aldrich

(DHQD)2Pyr

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C56H60N6O4
CAS Number:
149725-81-5
Molecular Weight:
881.11
MDL number:
MFCD00198108
UNSPSC Code:
12352005
PubChem Substance ID:
24866252
NACRES:
NA.22

Quality Level

100

Assay

97%

optical activity

[α]20/D −390°, c = 1.2 in methanol

mp

247-250 °C (lit.)

functional group

phenyl

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

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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.

Legal Information

Sold under license from Rhodia Pharma Solutions.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCH5092
MKBZ0926V
MKBN4716V
MKBF9764V
MKBF9764

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Total synthesis of the protein phosphatase inhibitor okadaic acid.
Ley SV, et al.
Journal of the Chemical Society. Perkin Transactions 1, 23, 3907-3912 (1998)
Stereocontrolled conversion of quinine into 10 (R), 11-dihydroxydihydroquinine via the sharpless osmylation process.
Zheng T, et al.
The Journal of Organic Chemistry, 66(4), 1509-1511 (2011)
Enantioselective organocatalytic allylic amination.
Journal of the American Chemical Society, 127(33), 11614-11615 (2005)

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