Bromide ion → HCID 13871700, compound

HRID 451351Notes

Reaction equation

HRID 451351 reaction equation
[CH2:1]1[O:8][C@@H:7]2[O:9][C@H:2]1[C@@H:3]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@@H:4]1[O:6][C@@H:5]12.[Br-].C([OH:21])C>>[CH2:11]([O:10][C@@H:3]1[C@H:2]2[CH2:1][O:8][C@H:7]([O:9]2)[C@H:5]([OH:21])[C@H:4]1[OH:6])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 3

HCID 259Bromide ionHCID 702EthanolHCID 11031793.beta.-D-Mannopyranose, 1,6:2,3-dianhydro-4-O-(phenylmethyl)-

Product 1

HCID 13871700HCID 13871700, compound

Procedure

Briefly, Jespersen first described synthesis of IFG in a six step synthesis starting from 1,6:2,3-dianhydro-4-O-benzyl-β-D-mannopyranose. This method employed introducing a hydroxymethyl group at C-7 by epoxide opening with vinylmagensium bromide, followed by ozonolysis in ethanol to give 1,6-anhydro-4-O-benzyl-β-D-glucopyranose. Hydrolysis of the anhydro bond with sulfuric acid and oxidative carbon chain cleavage provided a pentodialdose, which was cyclized by reductive amination with ammonia to produce the 4-O-benzyl derivative of IFG. The protecting group was removed by hydrogenation under acid conditions (hydrogen and palladium-on-carbon) to produce the HCl salt of IFG.

Workup

  1. customBriefly, Jespersen first described synthesis of IFG
  2. customin a six step synthesis

Sources & evidence

ORD record
ord-0c3304b089c14fc581873f0279eb108c
Source dataset
uspto-grants-2013_07
Patent number
US08487110B2

Reaction notes

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