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

HRID 1488241ノート

反応式

HRID 1488241 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e999d4fe37b146e59fe28d342eeb09a5
出典データセット
uspto-grants-2016_08
特許番号
US09427475B2

反応ノート

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