HCID 131736860, compound → HCID 131736859, compound

HRID 1488264Notes

Reaction equation

HRID 1488264 reaction equation
C(OC([N:11]([CH2:28][CH2:29][O:30][C@H:31]1[O:50][C@H:49]([CH2:51][O:52][C@H:53]2[O:61][C@H:60]([CH2:62][OH:63])[C@@H:58]([OH:59])[C@H:56]([OH:57])[C@@H:54]2[OH:55])[C@@H:47]([OH:48])[C@H:34]([O:35][C@H:36]2[O:44][C@H:43]([CH2:45][OH:46])[C@@H:41]([OH:42])[C@H:39]([OH:40])[C@@H:37]2[OH:38])[C@@H:32]1[OH:33])[C@H:12]([C:18]([O:20]CC1C=CC=CC=1)=[O:19])[CH2:13][CH2:14][C:15](=[O:17])[NH2:16])=O)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].O>[C@H:36]1([O:35][C@H:34]2[C@H:47]([OH:48])[C@@H:49]([CH2:51][O:52][C@H:53]3[O:61][C@H:60]([CH2:62][OH:63])[C@@H:58]([OH:59])[C@H:56]([OH:57])[C@@H:54]3[OH:55])[O:50][C@H:31]([O:30][CH2:29][CH2:28][NH:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][C:15](=[O:17])[NH2:16])[C@H:32]2[OH:33])[O:44][C@H:43]([CH2:45][OH:46])[C@@H:41]([OH:42])[C@H:39]([OH:40])[C@@H:37]1[OH:38]

Participants

4

Reactant 1

HCID 131736860HCID 131736860, compound

Product 1

HCID 131736859HCID 131736859, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 962WaterSolvent

Procedure

A mixture of benzyl N2-[(benzyloxy)carbonyl]-N-{2-[(α-D-mannopyranosyl-(1→3)-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranosyl)oxy]ethyl}-L-glutaminate (1.41 g, 1.57 mmol) and Pearlman's catalyst (110 mg, 0.157 mmol) in H2O (30 mL) was agitated under 50 Psi H2 on a Parr shaker at room temperature. After 16 hours, catalyst was filtered off and the filtrate was freeze-dried to give the title compound. 1H NMR (D2O) δ 5.07 (s, 1H), 4.87 (s, 1H), 4.81 (s, 1H), 4.08-3.55 (m, 22H), 3.41-3.36 (m, 1H), 2.32 (t, J=7.5, 2H), 2.10-2.06 (m, 2H).

Workup

  1. filtrationcatalyst was filtered off
  2. customthe filtrate was freeze-dried

Sources & evidence

ORD record
ord-9ac314445b4d467b8c651ff908fd7c9e
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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