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

HRID 1488241노트

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HRID 1488241 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e999d4fe37b146e59fe28d342eeb09a5
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09427475B2

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