D-(-)-Fructose → HCID 11677410, compound

HRID 1169868Notes

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])[CH:24]=[CH:23][C:22]([CH3:29])([CH3:28])[C:21](=[O:30])[C@H:20]([CH3:31])[C@@H:19]([OH:32])[C@@H:18]([CH3:33])[CH2:17][CH2:16][CH2:15][CH:14]=[CH:13][CH2:12]3)=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:34].[OH:35]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])[CH:24]=[CH:23][C:22]([CH3:28])([CH3:29])[C:21](=[O:30])[C@H:20]([CH3:31])[C@@H:19]([OH:32])[C@@H:18]([CH3:33])[CH2:17][CH2:16][CH2:15][C@H:14]4[C@@H:13]([O:35]4)[CH2:12]3)=[CH:10][C:5]=2[N:4]=[C:3]1[CH3:34]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 55 (40 mg, 0.0857 mmol) in 1.3 mL CH3CN/DMM—1/1 at rt were added successively 0.8 mL of a buffer solution (Na2B4O7.10 H2O [0.05M] in Na2EDTA [4.10−4M]), BU4N(HSO4) (1.2 mg, 0.003 mmol) and fructose-derived ketone (17.7 mg, 0.0685 mmol). The reaction mixture is cooled to 0° C. and were added separately, in a same time over 1 h30, Oxone® (73.8 mg, 0.120 mmol) in 1 mL Na2EDTA and K2CO3 (68.7 mg, 0.497 mmol) in 1 mL H2O. The solution is stirred 3 h 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 of crude product by prep-HPLC afforded 56, 50% conversion in a 8/1 ratio.

Workup

customis quenched with H2O
extractionextracted 3 times with 10 mL AcOEt
dry with materialThe combined organic layers are dried (MgSO4)
concentrationconcentrated in vacuum
customPurification of crude product

Sources & evidence

ORD record: ord-9d9e91bd9f9d47bd9dcc90a1e222093f
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825141B2

Reaction notes

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