Hydrogen Bromide → HCID 10962107, compound

HRID 29738Notes

Reaction equation

HRID 29738 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:13]([CH3:32])[O:12][CH:10]1[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:33]([C:36]1[CH:44]=[CH:43][C:39]([C:40]([O-:42])=[O:41])=[CH:38][CH:37]=1)([O-:35])=[O:34].[BrH:45]>C(Cl)Cl>[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:13]([CH3:32])[O:12][CH:10]1[OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[N+:33]([C:36]1[CH:37]=[CH:38][C:39]([C:40]([O-:42])=[O:41])=[CH:43][CH:44]=1)([O-:35])=[O:34].[CH2:1]([O:8][C@H:9]1[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:13]([CH3:32])[O:12][C@H:10]1[Br:45])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 86592297HCID 86592297, compound

Product 2

HCID 10962107HCID 10962107, compoundHCID 86592297HCID 86592297, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Similarly, treatment of the β-isomer of the fucopyranosyl-p-nitrobenzoate (compound 8) (583 mg, 1 mmol) with a saturated solution of HBr in CH2Cl2 (5 mL) for 30 min at 5° C. furnished the α-fucopyranosyl bromide (550 mg). The NMR spectrum of this product was identical with that of α-bromide obtained earlier from the α-fucopyranosyl p-nitrobenzoate. However, due to the instability of the bromide, it was used as such immediately for the next step. 1H-NMR (CDCl3): 1.17 (d, 3H, J=6.45 Hz, CH3), 3.6-4.2 (m, OCH), 4.8-5.02 (m, OCH2), 6.53 (d, 1H, OCHBr), 7.2-7.5 (15H, Ar—H); 13C-NMR (CDCl3): 16.61 (CH3), 72.36 (OCH), 73.23 (OCH2), 74.00 (OCH2), 75.59 (OCH2), 76.57 (OCH), 74.49 (OCH), 80.02 (OCH), 95.26 (OCHBr), 127.97, 128.09, 128.23, 128.32, 128.43, 128.75, 128.86 (aromatic carbons).

Sources & evidence

ORD record
ord-ddb9d66706404fae8c1c21913159ddb6
Source dataset
uspto-grants-2008_09
Patent number
US07422733B2

Reaction notes

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