Tetrahydrofuran → HCID 86598497, compound

HRID 1375974Notes

Reaction equation

HRID 1375974 reaction equation
CCCCCC.[CH2:7]([Li])CCC.[CH2:12]([O:19][C@@H:20]1[C@@H:25]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@H:24]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@@H:23]([CH2:42][O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[O:22][C@H:21]1[C:51]1[CH:56]=[C:55]([CH2:57][O:58][CH3:59])[CH:54]=[C:53](Br)[CH:52]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Cl-].[NH4+].C1C[O:66][CH2:65]C1>CN(C=O)C>[CH3:7][C:54]1[C:55]([CH2:57][O:58][CH3:59])=[CH:56][C:51]([C@H:21]2[C@H:20]([O:19][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C@@H:25]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:42]([O:43][CH2:44][C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C@@H:23]([CH2:24][O:34][CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[O:22]2)=[CH:52][C:53]=1[CH:65]=[O:66]

Participants

7

Reactant 5

HCID 8028TetrahydrofuranHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 58786221HCID 58786221, compoundHCID 178418339Butyllithium

Product 1

HCID 86598497HCID 86598497, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 1.6 M n-hexane solution of n-butyl lithium (14.0 ml) was added dropwise to a solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-bromo-5-(methoxymethyl)phenyl]-D-glucitol (7.8 g) in THF (5.0 ml) at −78° C. and the mixture was stirred for 30 minutes. DMF (1.0 ml) was added dropwise to the reaction mixture and the mixture was stirred for four hours. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain methyl 3-methoxymethyl-5-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]-tetrahydro-2H-pyran-2-yl]benzaldehyde (2.6 g).

Workup

  1. stirringthe mixture was stirred for four hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1d2085f03657498d9153cf035159e364
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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