HCID 131736865, compound → HCID 131736867, compound

HRID 1488271Notes

Reaction equation

HRID 1488271 reaction equation
[C@H:1]1([O:12][C@H:13]2[C@H:18]([O:19]CC3C=CC=CC=3)[C@@H:17]([CH2:27][O:28][C@H:29]3[O:37][C@H:36]([CH2:38][OH:39])[C@@H:34]([OH:35])[C@H:32]([OH:33])[C@@H:30]3[OH:31])[O:16][C@@H:15]([O:40][CH2:41][CH2:42][NH:43]C(=O)OCC3C=CC=CC=3)[C@@H:14]2[OH:54])[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:18]([OH:19])[C@@H:17]([CH2:27][O:28][C@H:29]3[O:37][C@H:36]([CH2:38][OH:39])[C@@H:34]([OH:35])[C@H:32]([OH:33])[C@@H:30]3[OH:31])[O:16][C@@H:15]([O:40][CH2:41][CH2:42][NH2:43])[C@@H:14]2[OH:54])[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 131736865HCID 131736865, compound

Product 1

HCID 131736867HCID 131736867, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of benzyl (2-{[α-D-mannopyranosyl-(1→3)-[α-D-mannopyranosyl-(1→6)]-4-O-benzyl-β-D-glucopyranosyl]oxy}ethyl)carbamate (0.96 g, 1.244 mmol) and Pd/C (124 mmol) in water (20 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 C20H37NO16 547.21, observed m/e: 548.29 [M+1]; Rt=0.87 min. 1H NMR (D2O) δ 5.20-5.19 (1H, m), 4.88-4.87 (1H, m), 4.51-4.49 (1H, m), 4.05 (1H, m), 4.00-3.90 (4H, m), 3.85-3.70 (9H, m), 3.70-3.60 (5H, m), 3.40-3.30 (1H, m), 3.05-3.00 (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-812173e4aba44ccdab5298836b0733da
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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