HCID 58843587, compound → HCID 58843591, compound

HRID 501899Notes

Reaction equation

HRID 501899 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@H:10]1[C:40]1[CH:45]=[C:44]([CH2:46][OH:47])[CH:43]=[C:42]([F:48])[CH:41]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[O:11][C@H:10]1[C:40]1[CH:45]=[C:44]([CH:43]=[C:42]([F:48])[CH:41]=1)[CH:46]=[O:47])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 58843587HCID 58843587, compound

Product 1

HCID 58843591HCID 58843591, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

Manganese dioxide (740 mg) was added to a solution of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-fluoro-5-(hydroxylmethyl)phenyl]-D-glucitol (0.5 g) in chloroform (10 ml), and the mixture was stirred for 24 hours. After filtration through celite, washing with chloroform was carried out, and the filtrate was concentrated. The resulting residue was dried to obtain 3-(-2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-fluorobenzaldehyde (0.4 g).

Workup

  1. filtrationAfter filtration through celite
  2. washwashing with chloroform
  3. concentrationthe filtrate was concentrated
  4. customThe resulting residue was dried

Sources & evidence

ORD record
ord-c94e4ab4363f4a2eab6b9845c7497b16
Source dataset
uspto-grants-2010_08
Patent number
US07772407B2

Reaction notes

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