HCID 131736876, compound → HCID 131736875, compound

HRID 1488306Notes

Reaction equation

HRID 1488306 reaction equation
[C@@H:1]1([O:11][CH2:12][CH2:13][N:14]([CH2:34][CH2:35][O:36][C@@H:37]2[O:45][C@@H:44]([CH3:46])[C@@H:42]([OH:43])[C@@H:40]([OH:41])[C@@H:38]2[OH:39])[CH2:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26]CC2C=CC=CC=2)=[O:25])=[O:17])[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]1[OH:3]>O.[Pd]>[C@@H:37]1([O:36][CH2:35][CH2:34][N:14]([CH2:13][CH2:12][O:11][C@@H:1]2[O:9][C@@H:8]([CH3:10])[C@@H:6]([OH:7])[C@@H:4]([OH:5])[C@@H:2]2[OH:3])[CH2:15][C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:17])[O:45][C@@H:44]([CH3:46])[C@@H:42]([OH:43])[C@@H:40]([OH:41])[C@@H:38]1[OH:39]

Participants

4

Reactant 1

HCID 131736876HCID 131736876, compound

Product 1

HCID 131736875HCID 131736875, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a solution of benzyl 6-(2-(bis(2-[(α-L-fucopyranosyl)oxy)ethyl)amino)acetamido)hexanoate (40 mg, 0.061 mmol) in water (5 ml), was added Pd/C (30.5 mg, 0.029 mmol). The reaction was stirred under H2 balloon for 18 hr. UPLC indicated formation of desired product. The above solution was diluted with MeOH (5 mL), filtered through a pad of celite, concentrated and lyo to give the titled compound as colorless syrup (20 mg, 6.1%). UPLC Method B: m/e=569.3191 [M+1]; Rt=1.93 min.

Sources & evidence

ORD record
ord-4b64ec576daa407ebccc67db8fdda995
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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