2-azidoethyl 3-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside → 2-aminoethyl 3-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside

HRID 1488245Notes

Reaction equation

[C@H:1]1([O:12][C@H:13]2[C@H:24]([OH:25])[C@@H:23]([CH2:26][OH:27])[O:22][C@H:15]([O:16][CH2:17][CH2:18][N:19]=[N+]=[N-])[C@H:14]2[OH:28])[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.CO.[Pd]>[C@H:1]1([O:12][C@H:13]2[C@H:24]([OH:25])[C@@H:23]([CH2:26][OH:27])[O:22][C@H:15]([O:16][CH2:17][CH2:18][NH2:19])[C@H:14]2[OH:28])[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

Conditions

Temperature: 25 °C

Procedure

In a 50 mL round bottom flask, 2-azidoethyl 3-O-α-D-mannopyranosyl-α-D-mannopyranoside (139 mg, 0.338 mmol) was dissolved in water/CH3OH (v/v 1:1, 5 mL). To the above solution was added Pd/C (10%, 36 mg, 0.034 mmol). The reaction mixture was stirred at 25° C. 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. LC-MS Method A: m/e=386.08 [M+1]; Rt=0.24 min.

Workup

filtrationThe mixture was filtered through a pad of Celite
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-c442b232eaa74f6eb411c260861e6386
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09427475B2

Reaction notes

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