2-azidoethyl 2,4-di-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside → 2-azidoethyl 3-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside

HRID 1488244Notes

Reaction equation

C([O:9][C@H:10]1[C@@H:21]([O:22][C@H:23]2[O:55][C@H:54]([CH2:56][O:57]C(=O)C3C=CC=CC=3)[C@@H:44]([O:45]C(=O)C3C=CC=CC=3)[C@H:34]([O:35]C(=O)C3C=CC=CC=3)[C@@H:24]2[O:25]C(=O)C2C=CC=CC=2)[C@H:20]([O:66]C(=O)C2C=CC=CC=2)[C@@H:19]([CH2:75][OH:76])[O:18][C@@H:11]1[O:12][CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])(=O)C1C=CC=CC=1.O(C)[Na]>CO>[C@H:23]1([O:22][C@H:21]2[C@H:20]([OH:66])[C@@H:19]([CH2:75][OH:76])[O:18][C@H:11]([O:12][CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])[C@H:10]2[OH:9])[O:55][C@H:54]([CH2:56][OH:57])[C@@H:44]([OH:45])[C@H:34]([OH:35])[C@@H:24]1[OH:25]

Participants

Conditions

Temperature: 25 °C

Procedure

In a 50 mL round bottom flask was added 2-azidoethyl 2,4-di-O-benzoyl-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-D-mannopyranoside (350 mg, 0.338 mmol) and CH3OH (5 mL). To the above solution was added NaOCH3 (conc) dropwise till pH >10. The reaction mixture was allowed to stir at 25° C. for 6 hr. To the above solution was added Dowex H+(50W×8-200) resin till pH ˜7. The solid resin was filtered off and the filtrate was concentrated to give the title compound. LC-MS Method A: m/e=434.00 [M+1]; Rt=0.44 min.

Workup

additionTo the above solution was added Dowex H+(50W×8-200) resin till pH ˜7
filtrationThe solid resin was filtered off
concentrationthe filtrate was concentrated

Sources & evidence

ORD record: ord-13ac546741284d2bb6aa207ee3760edb
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09427475B2

Reaction notes

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