HCID 131736868, compound → HCID 131736870, compound

HRID 1488276Notes

Reaction equation

HRID 1488276 reaction equation
[C@H:1]1([O:12][C@H:13]2[C@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:23]([CH2:33][O:34][C@H:35]3[O:43][C@H:42]([CH2:44][OH:45])[C@@H:40]([OH:41])[C@H:38]([OH:39])[C@@H:36]3[OH:37])[O:22][C@@H:15]([O:16][CH2:17][CH2:18][N:19]=[N+]=[N-])[C@@H:14]2[F:46])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3]>O.[Pd]>[C@H:1]1([O:12][C@H:13]2[C@H:24]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C@@H:23]([CH2:33][O:34][C@H:35]3[O:43][C@H:42]([CH2:44][OH:45])[C@@H:40]([OH:41])[C@H:38]([OH:39])[C@@H:36]3[OH:37])[O:22][C@@H:15]([O:16][CH2:17][CH2:18][NH2:19])[C@@H:14]2[F:46])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

4

Reactant 1

HCID 131736868HCID 131736868, compound

Product 1

HCID 131736870HCID 131736870, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-azidoethyl α-D-mannopyranosyl-(1→3)-[α-D-mannopyranosyl-(1→6)]-4-O-benzyl-2-deoxy-2-fluoro-β-D-glucopyranoside (1.77 g, 2.66 mmol) and Pd/C (0.133 mmol) in water (30 mL) was allowed to stir under a balloon of H2 at rt for 16 h. The catalyst was filtered off and washed with H2O (3×10 mL). The Titrate was concentrated to give the title compound. UPLC Method B: calculated for C20H36FNO15 549.21, observed m/e: 550.29 [M+1]; Rt=0.86 min. 1H NMR (D2O) δ 5.16-5.14 (1H, m), 4.88-4.86 (1H, m), 4.80-4.76 (1H, m), 4.30-4.16 (1H, m), 4.06-4.03 (1H, m), 3.98-3.88 (4H, m), 3.86-3.72 (9H, m), 3.70-3.62 (5H, m), 2.94-2.88 (2H, m).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with H2O (3×10 mL)
  3. concentrationThe Titrate was concentrated

Sources & evidence

ORD record
ord-d2d426134a9749b59e8a08ec12289c43
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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