Trityl chloride → 2-azidoethyl 2,4-di-O-benzoyl-6-O-trityl-beta-D-mannopyranoside

HRID 1488241Notes

Reaction equation

HRID 1488241 reaction equation
[C:1]([O:9][C@H:10]1[C@@H:21]([OH:22])[C@H:20]([O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:19]([CH2:32][OH:33])[O:18][C@@H:11]1[O:12][CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@H]1(O[C@H]2[C@H](O)[C@@H](CO[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)O[C@H](OCCN)[C@H]2O)O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O.[C:71](Cl)([C:84]1[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=1)([C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=1)[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:1]([O:9][C@H:10]1[C@@H:21]([OH:22])[C@H:20]([O:23][C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:19]([CH2:32][O:33][C:71]([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)([C:84]2[CH:85]=[CH:86][CH:87]=[CH:88][CH:89]=2)[C:78]2[CH:79]=[CH:80][CH:81]=[CH:82][CH:83]=2)[O:18][C@H:11]1[O:12][CH2:13][CH2:14][N:15]=[N+:16]=[N-:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 11590639(2S,3S,4S,5S,6R)-2-(2-azidoethoxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3,5-diyl dibenzoateHCID 117136792-Aminoethyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside

Product 1

HCID 1180057332-azidoethyl 2,4-di-O-benzoyl-6-O-trityl-beta-D-mannopyranoside

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

In a 250 ml round bottom flask, 2-azidoethyl 2,4-di-O-benzoyl-α-D-mannopyranoside (1.0 g, 2.186 mmol; See WO 2010/088294 A1, incorporated herein by reference) was dissolved in pyridine (50 mL). To the above solution was added DMAP (13 mg, 0.109 mmol) followed by trityl chloride (762 mg, 2.73 mmol). After stirring at 80° C. for 18 hr, the reaction mixture was concentrated. The residue was purified by flash chromatography on silica gel (40 g), eluting with 0-50% EtOAc in hexanes to give the title compound. UPLC Method C: m/e=722.2955, [M+Na]; Rt=4.50. 1H NMR (CDCl3) δ 7.0-8.3 (m, 25H), 5.8 (t, 1H), 5.5(m, 1H), 5.2 (s, 1H), 4.3 (m, 1H), 4.1 (m, 2H), 4.0 (m, 1H), 3.5 (m, 1H), 3.4 (m, 2H), 3.2 (dd, 1H), 2.7 (d, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customThe residue was purified by flash chromatography on silica gel (40 g)
  3. washeluting with 0-50% EtOAc in hexanes

Sources & evidence

ORD record
ord-e999d4fe37b146e59fe28d342eeb09a5
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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