N-bromobutanimide → 2,3,4,6-Tetra-O-benzyl-alpha-D-galactopyranosyl Fluoride

HRID 1510175Notes

Reaction equation

[CH2:1]([O:8][C@@H:9]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:19]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:18][C@H:10]1SC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(S(F)(F)[F:53])CC)C.BrN1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C@@H:9]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:19]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:18][C@@H:10]1[F:53])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -15 °C

Procedure

To a solution of 10 (10.0 g, 15.82 mmol, 1 eq) in dry CH2Cl2 (191 mL) under argon at −15° C. were added diethylaminosulfur trifluoride (3.14 mL, 23.73 mmol, 1.5 eq) and, after 2 min, N-bromosuccinimide (3.66 g, 20.57 mmol, 1.3 eq). After being stirred at −15° C. for 30 min the reaction was diluted with CH2Cl2 (420 mL) and poured into a cold saturated aqueous NaHCO3 solution (195 mL). The organic layer was dried over MgSO4 and concentrated. Purification by flash chromatography on silica gel (petroleum ether/EtOAc 94:6) afforded 11 as viscous syrup (6.3 g, 73%).

Workup

dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated
customPurification by flash chromatography on silica gel (petroleum ether/EtOAc 94:6)

Sources & evidence

ORD record: ord-1c29419f07504d2ab5eb1c6bfcd3f456
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211859B2

Reaction notes

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