Cornforth reagent → HCID 86596449, compound

HRID 1828686Notes

Reaction equation

HRID 1828686 reaction equation
[C:1]([NH:8][CH2:9][C@H:10]1[O:16][C@H:13]([CH2:14][OH:15])[C@@H:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:11]1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:34].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CN(C=O)C.CCOC(C)=O>[C:1]([NH:8][CH2:9][C@H:10]1[O:16][C@H:13]([C:14]([OH:34])=[O:15])[C@@H:12]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:11]1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 2724130Cornforth reagentHCID 11212935HCID 11212935, compound

Product 1

HCID 86596449HCID 86596449, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The product from step 5 was dissolved in dry DMF and cooled to 0° C. Pyridinium dichromate (PDC, 4 molar equiv) was added portion wise and the reaction mixture was stirred at room temperature for 12 h. It was then diluted with EtOAc, washed with saturated aqueous CuSO4, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. Purification by silica gel column chromatography gave the required N-Boc-6-amino-2,5-anhydro-3,4-di-O-benzyl-6-deoxy-D-mannonic acid in 77% yield.

Workup

  1. washwashed with saturated aqueous CuSO4, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-25269427a25945b2b8a5d8759eadb67a
Source dataset
uspto-grants-2006_06
Patent number
US07060678B2

Reaction notes

Loading…