D-Maltotriose Peracetate → Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(a1-4)a-Glc1Br2Ac3Ac6Ac

HRID 74845Notes

Reaction equation

[CH3:1][C:2]([O:4][CH2:5][C@H:6]1[O:11][C@H:10]([O:12][C@H:13]2[C@H:18]([O:19][C:20]([CH3:22])=[O:21])[C@@H:17]([O:23][C:24]([CH3:26])=[O:25])[CH:16](OC(C)=O)[O:15][C@@H:14]2[CH2:31][O:32][C:33]([CH3:35])=[O:34])[C@H:9]([O:36][C:37]([CH3:39])=[O:38])[C@@H:8]([O:40][C:41]([CH3:43])=[O:42])[C@@H:7]1[O:44][C@H:45]1[O:50][C@H:49]([CH2:51][O:52][C:53]([CH3:55])=[O:54])[C@@H:48]([O:56][C:57]([CH3:59])=[O:58])[C@H:47]([O:60][C:61]([CH3:63])=[O:62])[C@H:46]1[O:64][C:65]([CH3:67])=[O:66])=[O:3].[BrH:68].CC(O)=O>C(Cl)Cl>[C:65]([O:64][C@@H:46]1[C@@H:47]([O:60][C:61](=[O:62])[CH3:63])[C@H:48]([O:56][C:57](=[O:58])[CH3:59])[C@@H:49]([CH2:51][O:52][C:53](=[O:54])[CH3:55])[O:50][C@@H:45]1[O:44][C@@H:7]1[C@@H:6]([CH2:5][O:4][C:2](=[O:3])[CH3:1])[O:11][C@H:10]([O:12][C@@H:13]2[C@@H:14]([CH2:31][O:32][C:33](=[O:34])[CH3:35])[O:15][C@H:16]([Br:68])[C@H:17]([O:23][C:24](=[O:25])[CH3:26])[C@H:18]2[O:19][C:20](=[O:21])[CH3:22])[C@H:9]([O:36][C:37](=[O:38])[CH3:39])[C@H:8]1[O:40][C:41](=[O:42])[CH3:43])(=[O:66])[CH3:67]

Participants

Conditions

Temperature: 0 °C

Procedure

Maltotriose peracetate (71)36 (200 mg, 207 μmol) was taken up in DCM (1 mL) and 33% HBr/HOAc (0.7 mL) at 0° C. The mixture was stirred at 0° C. for four hours. The solution was diluted with DCM and washed with ice-water (×2), NaHCO3 (sat.) (×2) and brine (×1), before being dried (Na2SO4) and the solvent evaporated to yield the bromide 72 as white solid which was reacted on without further purification or characterisation.

Workup

customat 0° C
washwashed with ice-water (×2), NaHCO3 (sat.) (×2) and brine (×1)
dry with materialbefore being dried (Na2SO4)
customthe solvent evaporated

Sources & evidence

ORD record: ord-152897acbd4f4b1cad29ca1cc4a352df
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828952B2

Reaction notes

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