1,2-Dichloroethane → EtOAc AcCN MeOH

HRID 1488262ノート

反応式

HRID 1488262 の反応式
[O:1]([CH2:12][CH2:13][NH2:14])[C@@H:2]1[O:10][C@@H](C)[C@@H](O)[C@@H](O)[C@@H:3]1O.[CH2:15](Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:13][CH2:12][O:1][C:2]([CH3:3])=[O:10].[C:12]([C:13]#[N:14])([CH3:15])=[O:1].[CH3:2][OH:1]

参加物

5

反応物 2

HCID 111,2-DichloroethaneHCID 10954744(2R,3S,4R,5S,6S)-2-(2-Aminoethoxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

生成物 1

HCID 131736857EtOAc AcCN MeOH

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of N-[(benzyl)carbonyl]-L-glutei acid (1.1 g, 3.91 mmol) and 2-amino ethyl α-L-fucopyranoside (2.026 g, 9.78 mmol) in DMF (10 mL) was added EDC (3.00 g, 15.64 mmol) and DMAP (0.048 g, 0.391 mmol). After stirring at rt for 24 hr, the reaction mixture was concentrated and the residue was purified by flash chromatography on silica gel (80 g), eluting with 100% EtOAc for 5 column volume and then isocratic EtOAc:AcCN:MeOH 6:1:1 to give the title compound. 1H NMR (CD3OD) δ 7.38-7.29 (m, 5H), 5.13-5.05 (m, 2H), 4.76 (s, 2H), 4.09 (dd, J=5.3, 8.6, 1H), 3.95-3.91 (m, 2H), 3.74-3.65 (m, 6H), 3.53-3.25 (m, 8H), 2.30 (t, J=7.5, 2H), 2.06-2.04 (m, 1H), 1.92-1.89 (m, 1H), 1.19 (d, J=6.5, 6H).

後処理

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography on silica gel (80 g)
  3. washeluting with 100% EtOAc for 5 column volume

出典と根拠

ORDレコード
ord-898a35cc7f384b32add5da09d1b826d2
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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