Mannitol → 2,5-anhydro-1-deoxy-1-(diethoxyphosphinyl)-1-fluoro-D-mannitol

HRID 2166293Notes

Reaction equation

HRID 2166293 reaction equation
C(O)[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[CH2:13]([O:15][P:16]([O:43][CH2:44][CH3:45])([CH:18]([F:42])[C@@H:19]1[O:39][C@H:38]([CH2:40][OH:41])[C@@H:29]([O:30]CC2C=CC=CC=2)[C@@H:20]1[O:21]CC1C=CC=CC=1)=[O:17])[CH3:14].C(O)[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.P([O-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[H][H]>CO.[OH-].[Pd+2].[OH-]>[CH2:13]([O:15][P:16]([O:43][CH2:44][CH3:45])([CH:18]([F:42])[C@H:19]1[O:39][C@H:38]([CH2:40][OH:41])[C@@H:29]([OH:30])[C@@H:20]1[OH:21])=[O:17])[CH3:14]

Participants

7

Reactant 4

HCID 6251MannitolHCID 3610038CID 3610038HCID 1317164832,5-anhydro-1-deoxy-1-(diethoxyphosphinyl)-1-fluoro-3,4-bis-O-(phenylmethyl)-D-glucitol D-glucitolHCID 178418361HCID 178418361, compound

Product 1

HCID 886091632,5-anhydro-1-deoxy-1-(diethoxyphosphinyl)-1-fluoro-D-mannitolYield 90%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 330 mg of 2,5-anhydro-1-deoxy-1-(diethoxyphosphinyl)-1-fluoro-3,4-bis-O-(phenylmethyl)-D-glucitol D-glucitol and D-mannitol, diphenyl phosphate mixture in 20 ml of methanol was hydrogenated over palladium hydroxide catalyst until hydrogen uptake ceased. Filtration and removal of the solvent gave a yellow oil. This oil was purified by flash chromatography taking 20 ml fractions Fractions 1-26 were eluted with 3% methanol in dichloromethane and after evaporation gave 135 mg of 2,5-anhydro-1-deoxy-1-(diethoxyphosphinyl)-1-fluoro-D-mannitol, 6-(diphenyl phosphate).

Workup

  1. filtrationFiltration and removal of the solvent
  2. customgave a yellow oil
  3. customThis oil was purified by flash chromatography
  4. washwere eluted with 3% methanol in dichloromethane
  5. customafter evaporation

Sources & evidence

ORD record
ord-b9c24b1e61e84ceab1c0c72a804821e8
Source dataset
uspto-grants-1990_07
Patent number
US04943629

Reaction notes

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