Trichloroacetonitrile → 3,4-Di-O-benzyl-2-O-levulinoyl-alpha-L-rhamnopyranosyl trichloroacetimidate

HRID 62288

反応式

[Cl:1][C:2]([Cl:6])([Cl:5])[C:3]#[N:4].C1CCN2C(=NCCC2)CC1.[CH2:18]([O:25][C@@H:26]1[C@@H:32]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:31]([CH3:41])[O:30][C@@H:28]([OH:29])[C@@H:27]1[O:42][C:43](=[O:49])[CH2:44][CH2:45][C:46]([CH3:48])=[O:47])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[Cl:1][C:2]([Cl:6])([Cl:5])[C:3](=[NH:4])[O:29][C@@H:28]1[O:30][C@@H:31]([CH3:41])[C@H:32]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C@@H:26]([O:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:27]1[O:42][C:43](=[O:49])[CH2:44][CH2:45][C:46]([CH3:48])=[O:47]

参加物

実験手順

Trichloroacetonitrile (1.3 mL, 13 mmol) and DBU (51 μL, 0.3 mmol) were added to a solution of the residue 211 (1.0 g, 2.3 mmol) in anhydrous DCM (6 mL) at 0° C. After 2 h, the mixture was concentrated. The residue was eluted from a column of silica gel with 3:1 cyclohexane-EtOAc and 0.2% Et3N to give 212 as a white foam (1.0 g, 95%); 1H NMR: δ 8.67 (s, 1H, NH), 7.40-7.30 (m, 10H, Ph), 6.19 (d, 1H, J1,2=1.9 Hz, H-1), 5.48 (dd, 1H, J1,2=2.0, J2,3=3.3 Hz, H-2), 4.95 (d, 1H, CH2Ph), 4.73 (d, 1H, CH2Ph), 4.66 (d, 1H, CH2Ph), 4.58 (d, 1H, CH2Ph), 4.51 (d, 1H, CH2Ph), 4.00 (dd, 1H, J3,4=9.5 Hz, H-3), 3.95 (dq, 1H, J4,5=9.6, J5,6=6.3 Hz, H-5), 3.52 (pt, 1H, H-4), 2.80 (m, 4H, Lev), 2.20 (s, 3H, Ac), 1.36 (d, 3H, H-6). Anal. Calcd for C27H30Cl3NO7.0.5H2O: C, 54.42; H, 5.24; N, 2.35. Found: C, 54.06; H, 5.06; 2.05.

後処理

concentrationthe mixture was concentrated
washThe residue was eluted from a column of silica gel with 3:1 cyclohexane-EtOAc and 0.2% Et3N

出典と根拠

ORDレコード: ord-81c6d510d0074720930d7a0ce6472097
出典データセット: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09446109B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

関連ノート