(S)-benzyl 2-{[(benzyloxy)carbonyl]amino}-5-[(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)amino]-5-oxopentanoate → (S)-2-amino-5-((2-((alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl)oxy)ethyl)amino)-5-oxopentanoic acid

HRID 1488266Notes

Reaction equation

HRID 1488266 reaction equation
C(OC([NH:11][C@@H:12]([CH2:23][CH2:24][C:25]([NH:27][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])=[O:26])[C:13]([O:15]CC1C=CC=CC=1)=[O:14])=O)C1C=CC=CC=1>O.[Pd]>[NH2:11][C@@H:12]([CH2:23][CH2:24][C:25]([NH:27][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])=[O:26])[C:13]([OH:15])=[O:14]

Participants

4

Reactant 1

HCID 131736861(S)-benzyl 2-{[(benzyloxy)carbonyl]amino}-5-[(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)amino]-5-oxopentanoate

Product 1

HCID 131736862(S)-2-amino-5-((2-((alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl)oxy)ethyl)amino)-5-oxopentanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of (S)-benzyl 2-{[(benzyloxy)carbonyl]amino}-5-[(2-{[α-D-mannopyranosyl-(1→3)-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranosyl]oxy}ethyl)amino]-5-oxopentanoate (1.0 g, 1.11 mmol) and Pd/C (118 mg, 0.111 mmol) in water (10 mL) was allowed to stir under a balloon of H2 at room temperature for 16 hours. The catalyst was filtered off and washed with H2O (3×10 mL). The filtrate was concentrated to give the title compound. UPLC Method B: calculated for C25H44N2O19 676.25, observed m/e: 677.21 [M+1]; Rt=0.86 min.

Workup

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

Sources & evidence

ORD record
ord-f7372509db1047f2a21d24eb1a2977e1
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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