HCID 11354944, compound → Kaempferol 3-O-(3′′,4′′-di-O-acetyl-α-L-rhamnopyranoside)

HRID 1821064Notes

Reaction equation

HRID 1821064 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]([O:19]CC2C=CC=CC=2)[CH:16]=[C:15]2[C:10]=1[C:11](=[O:65])[C:12]([O:41][C@@H:42]1[O:63][C@@H:62]([CH3:64])[C@H:57]([O:58][C:59](=[O:61])[CH3:60])[C@@H:52]([O:53][C:54](=[O:56])[CH3:55])[C@H:43]1[O:44]CC1C=CC=CC=1)=[C:13]([C:27]1[CH:32]=[CH:31][C:30]([O:33]CC3C=CC=CC=3)=[CH:29][CH:28]=1)[O:14]2)C1C=CC=CC=1>C1COCC1.CO.[OH-].[OH-].[Pd+2]>[CH3:64][C@@H:62]1[O:63][C@@H:42]([O:41][C:12]2[C:11](=[O:65])[C:10]3[C:15](=[CH:16][C:17]([OH:19])=[CH:18][C:9]=3[OH:8])[O:14][C:13]=2[C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=2)[C@H:43]([OH:44])[C@H:52]([O:53][C:54]([CH3:55])=[O:56])[C@H:57]1[O:58][C:59]([CH3:60])=[O:61]

Participants

4

Reactant 1

HCID 11354944HCID 11354944, compound

Product 1

HCID 10459196Kaempferol 3-O-(3′′,4′′-di-O-acetyl-α-L-rhamnopyranoside)

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A suspension containing 0.26 g (0.29 mmol) of 10 and 0.10 g of Pd(OH)2/C in 10 mL of 1:1 THF-MeOH was purged with H2 and maintained under a H2 atmosphere for 1 h. The reaction mixture was then diluted with ethyl acetate, filtered through a Celite pad and washed with ethyl acetate. The filtrate was concentrated under diminished pressure to give 1 as a tan solid: yield 0.14 g (94%); silica gel TLC Rf 0.35 (1:1:0.1 hexanes-ethyl acetate-methanol); [α]D17−106.5 (c 0.65, MeOH); 1H NMR (acetone-d6) δ 0.86 (d, 3H, J=6.3 Hz), 1.32 (br s, 1H), 2.01 (s, 3H), 2.06 (s, 3H), 3.54 (m, 1H), 4.48 (d, 1H, J=2.1 Hz), 5.12 (m, 1H), 5.23 (dd, 1H, J=9.9, 2.7 Hz), 5.61 (d, 1H, J=0.9 Hz), 6.32 (brs, 1H), 6.53 (brs, 1H), 7.09 (d, 2H, J=8.4 Hz), 7.90 (d, 2H, J=8.1 Hz), 9.44 (br s, 2H) and 12.62 (br s, 1H); 13C NMR (acetone-d6) δ 17.0, 20.2, 68.7, 70.5, 71.7, 94.1, 99.2, 101.5, 105.2, 115.9, 121.8, 131.1, 134.8, 157.5, 158.0, 160.5, 162.7, 164.6, 169.7, 170.1 and 178.5; mass spectrum (FAB), m/z 517.1345 (M+H)+ (C25H25O12 requires 517.1346).

Workup

  1. customwas purged with H2
  2. temperaturemaintained under a H2 atmosphere for 1 h
  3. additionThe reaction mixture was then diluted with ethyl acetate
  4. filtrationfiltered through a Celite pad
  5. washwashed with ethyl acetate
  6. concentrationThe filtrate was concentrated under diminished pressure

Sources & evidence

ORD record
ord-a485464a6a4e438eae7d6e1b19ced9a0
Source dataset
uspto-grants-2009_10
Patent number
US07605241B2

Reaction notes

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