D-(-)-Fructose → HCID 86620184, compound

HRID 1169867Notes

Reaction equation

HRID 1169867 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C@H:11]3[O:26][C:25](=[O:27])[CH2:24][C@H:23]([OH:28])[C:22]([CH3:30])([CH3:29])[C:21](=[O:31])[C@H:20]([CH3:32])[C@@H:19]([OH:33])[C@@H:18]([CH3:34])[CH2:17][CH2:16][CH2:15][CH:14]=[CH:13][CH2:12]3)=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:35].[OH:36]CC([C@H]([C@@H]([C@@H](CO)O)O)O)=O.OOS([O-])=O.[K+].C([O-])([O-])=O.[K+].[K+]>CC#N.C(N(CC([O-])=O)CC(O)=O)CN(CC([O-])=O)CC(O)=O.[Na+].[Na+].O>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][C:9]([C@H:11]3[O:26][C:25](=[O:27])[CH2:24][C@H:23]([OH:28])[C:22]([CH3:29])([CH3:30])[C:21](=[O:31])[C@H:20]([CH3:32])[C@@H:19]([OH:33])[C@@H:18]([CH3:34])[CH2:17][CH2:16][CH2:15][C@H:14]4[C@@H:13]([O:36]4)[CH2:12]3)=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:35]

Participants

8

Reactant 4

HCID 5984D-(-)-FructoseHCID 11430Potassium CarbonateHCID 11547580HCID 11547580, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 86620184HCID 86620184, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8759EDTA disodium saltSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 48 (24 mg, 0.0495 mmol) in 0.75 mL CH3CN/DMM—1/1 at rt were added successively 0.46 mL of a buffer solution (Na2B4O7.10 H2O [0.05M] in Na2EDTA [4.10−4M]), Bu4N(HSO4) (0.67 mg, 0.0019 mmol) and fructose-derived ketone (10.2 mg, 0.0396 mmol). The reaction mixture is cooled to 0° C. and were added separately, in a same time over 1 h30, Oxone® (42.6 mg, 0.089 mmol) in 0.6 mL Na2EDTA and K2CO3 (39.7 mg, 0.287 mmol) in 0.6 mL H2O. The solution is stirred 1 h30 at 0° C. and then is quenched with H2O, extracted 3 times with 10 mL AcOEt. The combined organic layers are dried (MgSO4) and concentrated in vacuum. Purification by flash column chromatography (Hexane/Acetone/MeOH—50/45/5) afforded 49 in a 8/1 ratio as white crystals.

Workup

  1. customis quenched with H2O
  2. extractionextracted 3 times with 10 mL AcOEt
  3. dry with materialThe combined organic layers are dried (MgSO4)
  4. concentrationconcentrated in vacuum
  5. customPurification by flash column chromatography (Hexane/Acetone/MeOH—50/45/5)

Sources & evidence

ORD record
ord-fbdfcd22ae0041d0aeed5178b9d436d3
Source dataset
uspto-grants-2010_11
Patent number
US07825141B2

Reaction notes

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