Pyridine → HCID 22842891, compound

HRID 466910Notes

Reaction equation

HRID 466910 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[C@H]1O[C@H](OC)[C@H](OCC2C=CC=CC=2)[C@@H](OCC2C=CC=CC=2)[C@@H]1OCC1C=CC=CC=1)C1C=CC=CC=1.[CH2:89]([O:96][C@@H:97]1[C@@H:102]([O:103][CH2:104][C:105]2[CH:110]=[CH:109][CH:108]=[CH:107][CH:106]=2)[C@H:101]([CH2:111][O:112][S:113]([C:116]([F:119])([F:118])[F:117])(=[O:115])=[O:114])[C@@H:100]([CH2:120][O:121][CH2:122][C:123]2[CH:128]=[CH:127][CH:126]=[CH:125][CH:124]=2)[O:99][C@@H:98]1[O:129][CH2:130][C@H:131]1[O:138][C@H:135]([O:136][CH3:137])[C@H:134]([O:139][CH2:140][C:141]2[CH:146]=[CH:145][CH:144]=[CH:143][CH:142]=2)[C@@H:133]([O:147][CH2:148][C:149]2[CH:154]=[CH:153][CH:152]=[CH:151][CH:150]=2)[C@@H:132]1[O:155][CH2:156][C:157]1[CH:162]=[CH:161][CH:160]=[CH:159][CH:158]=1)[C:90]1[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=1.OS(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH2:89]([O:96][C@@H:97]1[C@@H:102]([O:103][CH2:104][C:105]2[CH:106]=[CH:107][CH:108]=[CH:109][CH:110]=2)[C@H:101]([CH2:111][O:112][S:113]([C:116]([F:119])([F:117])[F:118])(=[O:115])=[O:114])[C@@H:100]([CH2:120][O:121][CH2:122][C:123]2[CH:128]=[CH:127][CH:126]=[CH:125][CH:124]=2)[O:99][C@@H:98]1[O:129][CH2:130][C@H:131]1[O:138][C@H:135]([O:136][CH3:137])[C@H:134]([O:139][CH2:140][C:141]2[CH:142]=[CH:143][CH:144]=[CH:145][CH:146]=2)[C@@H:133]([O:147][CH2:148][C:149]2[CH:154]=[CH:153][CH:152]=[CH:151][CH:150]=2)[C@@H:132]1[O:155][CH2:156][C:157]1[CH:162]=[CH:161][CH:160]=[CH:159][CH:158]=1)[C:90]1[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 22842890HCID 22842890, compoundHCID 86746300HCID 86746300, compound

Product 1

HCID 22842891HCID 22842891, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of dry pyridine (0.46 mL) in dry methylene chloride (40 mL) cooled to -15° C. is added trifluoromethanesulfonic anhydride (0.86 mL). The mixture is stirred during 15 min at -10° C., then methyl 6-O-(2,3,6-tri-O-benzyl-4-deoxy-4-hydroxymethyl-α-D-glucopyranosyl)2,3,4-tri-O-benzyl-α-D-glucopyranoside (2.36 g, 2.593 mmol) in methylene chloride (10 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 will be the expected triflate methyl 6-O-(2,3,6-tri-O-benzyl-4-deoxy-4-trifluoromethylsulfonyloxymethyl-α-D-glucopyranosyl)-2,3,4-tri-O-benzyl-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-a313f96199f7420aaca9efaddc63bd31
Source dataset
uspto-grants-1992_10
Patent number
US05157116

Reaction notes

Loading…