1,2-Dichloroethane → EtOAc AcCN MeOH

HRID 1488262노트

반응식

HRID 1488262 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 131736857EtOAc AcCN MeOH

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-898a35cc7f384b32add5da09d1b826d2
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09427475B2

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