Pyridine → HCID 22842888, compound

HRID 466899Notes

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](COCC2C=CC=CC=2)O[C@@H]1OC)C1C=CC=CC=1.[CH2:56]([O:63][C@@H:64]1[C@@H:71]([O:72][CH2:73][C:74]2[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=2)[C@@H:70]([O:80][S:81]([C:84]([F:87])([F:86])[F:85])(=[O:83])=[O:82])[C@@H:69]([CH2:88][O:89][CH2:90][C:91]2[CH:96]=[CH:95][CH:94]=[CH:93][CH:92]=2)[O:68][C@@H:65]1[O:66][CH3:67])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1.OS(C(F)(F)F)(=O)=O>C(Cl)Cl>[CH2:56]([O:63][C@@H:64]1[C@@H:71]([O:72][CH2:73][C:74]2[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=2)[C@@H:70]([O:80][S:81]([C:84]([F:86])([F:87])[F:85])(=[O:82])=[O:83])[C@@H:69]([CH2:88][O:89][CH2:90][C:91]2[CH:92]=[CH:93][CH:94]=[CH:95][CH:96]=2)[O:68][C@@H:65]1[O:66][CH3:67])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of dry pyridine (0.46 mL) in methylene chloride (17.5 mL) cooled to -15° C. is added trifluoromethane sulfonic anhydride (0.87 mL). The mixture is stirred during 15 min at -10° C., then methyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside (1.2 g, 2.58 mmol) in methylene chloride (5 mL) is added (N. Morishima, S. Koto, M. Oshima, A. Sugimoto and S. Zen, Bull. Chem. Soc. Jpn, 56, 2849 (1983)). The 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-O-trifluoromethylsulfonyl-α-D-galactopyranoside.

Workup

washThe mixture is washed with water
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure so as
customto afford an oil which

Sources & evidence

ORD record: ord-ad24f853872a4bc489e7c1421a4c2d91
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05157116

Reaction notes

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