Pyridine → HCID 53978061, compound

HRID 466900Notes

Reaction equation

HRID 466900 reaction equation
N1C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C(O[C@@H]1[C@@H](OCC2C=CC=CC=2)[C@H](CO)[C@@H](COCC2C=CC=CC=2)O[C@@H]1OC)C1C=CC=CC=1.[CH2:57]([O:64][C@@H:65]1[C@@H:72]([O:73][CH2:74][C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)[C@H:71]([CH2:81][O:82][S:83]([C:86]([F:89])([F:88])[F:87])(=[O:85])=[O:84])[C@@H:70]([CH2:90][O:91][CH2:92][C:93]2[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=2)[O:69][C@@H:66]1[O:67][CH3:68])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1.OS(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH2:57]([O:64][C@@H:65]1[C@@H:72]([O:73][CH2:74][C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)[C@H:71]([CH2:81][O:82][S:83]([C:86]([F:88])([F:89])[F:87])(=[O:84])=[O:85])[C@@H:70]([CH2:90][O:91][CH2:92][C:93]2[CH:94]=[CH:95][CH:96]=[CH:97][CH:98]=2)[O:69][C@@H:66]1[O:67][CH3:68])[C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 14602393HCID 14602393, compoundHCID 86746298HCID 86746298, compound

Product 1

HCID 53978061HCID 53978061, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of dry pyridine (0.45 mL) in methylene chloride (30 mL) cooled to -15° C. is added trifluoromethanesulfonic anhydride (0.84 mL). The mixture is stirred during 15 min at -10° C., then methyl 2,3,6-tri-O-benzyl-4-deoxy-4-hydroxymethyl-α-D-glucopyranoside (1.19 g, 2.49 mmol) in methylene chloride (5 mL) is added. The mixture is stirred during 1.5 h at -10° C. The reaction mixture is washed with water. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure so as to afford an oil which is the expected triflate methyl 2,3,6-tri-O-benzyl-4-deoxy-4-trifluoromethylsulfonyloxymethyl-α-D-glucopyranoside.

Workup

  1. stirringThe mixture is stirred during 1.5 h at -10° C
  2. washThe reaction mixture is washed with water
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure so as
  6. customto afford an oil which

Sources & evidence

ORD record
ord-527125b14abb4a83a5541f50290b6a9a
Source dataset
uspto-grants-1992_10
Patent number
US05157116

Reaction notes

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