N2-[(benzyloxy)carbonyl]-N6-[6-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)-6-oxohexanoyl]-N-(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)-L-lysinamide → N-{(5S)-5-amino-6-[(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)amino]-6-oxohexyl}-N'-{2-[(alpha-L-fucopyranosyl)oxy]ethyl}hexanediamide

HRID 1488260Notes

Reaction equation

HRID 1488260 reaction equation
C(OC([NH:11][C@H:12]([C:40]([NH:42][CH2:43][CH2:44][O:45][C@H:46]1[O:65][C@H:64]([CH2:66][O:67][C@H:68]2[O:76][C@H:75]([CH2:77][OH:78])[C@@H:73]([OH:74])[C@H:71]([OH:72])[C@@H:69]2[OH:70])[C@@H:62]([OH:63])[C@H:49]([O:50][C@H:51]2[O:59][C@H:58]([CH2:60][OH:61])[C@@H:56]([OH:57])[C@H:54]([OH:55])[C@@H:52]2[OH:53])[C@@H:47]1[OH:48])=[O:41])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:39])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][CH2:26][CH2:27][O:28][C@@H:29]1[O:37][C@@H:36]([CH3:38])[C@@H:34]([OH:35])[C@@H:32]([OH:33])[C@@H:30]1[OH:31])=[O:24])=O)C1C=CC=CC=1>O.[Pd]>[NH2:11][C@H:12]([C:40]([NH:42][CH2:43][CH2:44][O:45][C@H:46]1[O:65][C@H:64]([CH2:66][O:67][C@H:68]2[O:76][C@H:75]([CH2:77][OH:78])[C@@H:73]([OH:74])[C@H:71]([OH:72])[C@@H:69]2[OH:70])[C@@H:62]([OH:63])[C@H:49]([O:50][C@H:51]2[O:59][C@H:58]([CH2:60][OH:61])[C@@H:56]([OH:57])[C@H:54]([OH:55])[C@@H:52]2[OH:53])[C@@H:47]1[OH:48])=[O:41])[CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:39])[CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:25][CH2:26][CH2:27][O:28][C@@H:29]1[O:37][C@@H:36]([CH3:38])[C@@H:34]([OH:35])[C@@H:32]([OH:33])[C@@H:30]1[OH:31])=[O:24]

Participants

4

Reactant 1

HCID 131736856N2-[(benzyloxy)carbonyl]-N6-[6-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)-6-oxohexanoyl]-N-(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)-L-lysinamide

Product 1

HCID 117996338N-{(5S)-5-amino-6-[(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)amino]-6-oxohexyl}-N'-{2-[(alpha-L-fucopyranosyl)oxy]ethyl}hexanediamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

In a 100 mL flask, N2-[(benzyloxy)carbonyl]-N6-[6-({2-[(α-L-fucopyranosyl)oxy]ethyl}amino)-6-oxohexanoyl]-N-(2-{[α-D-mannopyranosyl-(1→3)-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranosyl]oxy}ethyl)-L-lysinamide (950 mg, 0.843 mmol) was dissolved in water (10 mL). The flask was degassed and filled with N2. To the resulting mixture was added Pd/C (10%, 179 mg, 0.169 mmol). The mixture was stirred under H2 balloon for 18 hr. The mixture was filtered through a pad of Celite, and the filtrate was concentrated to give the title compound. UPLC Method B: m/e=993.326 [M+1]; Rt=1.37 min.

Workup

  1. customThe flask was degassed
  2. additionfilled with N2
  3. filtrationThe mixture was filtered through a pad of Celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0d01f4cf494d4a40baf624aa9dd7d7d9
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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