Pyridine → HCID 18648382, compound

HRID 466904Notes

Reaction equation

HRID 466904 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](O[C@H]2O[C@H](COCC3C=CC=CC=3)[C@H](O)[C@H](OCC3C=CC=CC=3)[C@H]2OCC2C=CC=CC=2)[C@@H](COCC2C=CC=CC=2)O[C@@H]1OC)C1C=CC=CC=1.[CH2:88]([O:95][C@@H:96]1[C@@H:101]([O:102][CH2:103][C:104]2[CH:109]=[CH:108][CH:107]=[CH:106][CH:105]=2)[C@@H:100]([O:110][S:111]([C:114]([F:117])([F:116])[F:115])(=[O:113])=[O:112])[C@@H:99]([CH2:118][O:119][CH2:120][C:121]2[CH:126]=[CH:125][CH:124]=[CH:123][CH:122]=2)[O:98][C@@H:97]1[O:127][C@@H:128]1[C@@H:135]([CH2:136][O:137][CH2:138][C:139]2[CH:144]=[CH:143][CH:142]=[CH:141][CH:140]=2)[O:134][C@H:131]([O:132][CH3:133])[C@H:130]([O:145][CH2:146][C:147]2[CH:152]=[CH:151][CH:150]=[CH:149][CH:148]=2)[C@H:129]1[O:153][CH2:154][C:155]1[CH:160]=[CH:159][CH:158]=[CH:157][CH:156]=1)[C:89]1[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=1.OS(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH2:88]([O:95][C@@H:96]1[C@@H:101]([O:102][CH2:103][C:104]2[CH:105]=[CH:106][CH:107]=[CH:108][CH:109]=2)[C@@H:100]([O:110][S:111]([C:114]([F:115])([F:116])[F:117])(=[O:112])=[O:113])[C@@H:99]([CH2:118][O:119][CH2:120][C:121]2[CH:126]=[CH:125][CH:124]=[CH:123][CH:122]=2)[O:98][C@@H:97]1[O:127][C@@H:128]1[C@@H:135]([CH2:136][O:137][CH2:138][C:139]2[CH:140]=[CH:141][CH:142]=[CH:143][CH:144]=2)[O:134][C@H:131]([O:132][CH3:133])[C@H:130]([O:145][CH2:146][C:147]2[CH:152]=[CH:151][CH:150]=[CH:149][CH:148]=2)[C@H:129]1[O:153][CH2:154][C:155]1[CH:156]=[CH:157][CH:158]=[CH:159][CH:160]=1)[C:89]1[CH:94]=[CH:93][CH:92]=[CH:91][CH:90]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 53653499HCID 53653499, compoundHCID 86746299HCID 86746299, compound

Product 1

HCID 18648382HCID 18648382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of dry pyridine (0.49 mL) in dry methylene chloride (40 mL) cooled to -15° C. is added trifluoromethanesulfonic anhydride (0.91 mL). The mixture is stirred during 15 min at -10° C., then methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-α-D-galactopyranosyl)-α-D-glucopyranoside (2.428 g, 2.71 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 4-O-(2,3,6-tri-O-benzyl-4-O-tri-fluoromethylsulfonyl-α-D-galactopyranosyl)-2,3,6-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-e4b476730a2c4da4af5f5cf5d7ab1025
Source dataset
uspto-grants-1992_10
Patent number
US05157116

Reaction notes

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