Boron trifluoride etherate → p-Methylphenyl 3,4,6tri-o-acetyl-2-deoxy-2-phthalimido-1-thio-beta-d-galactopyranoside

HRID 1862751ノート

反応式

HRID 1862751 の反応式
C(O[C@@H:5]1[O:18][C@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[C@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@H:7]([O:8][C:9](=[O:11])[CH3:10])[C@H:6]1[N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])(=O)C.[C:35]1(C)[C:40]([SH:41])=[CH:39][CH:38]=[CH:37][CH:36]=1.B(F)(F)F.[CH3:47]COCC>C(Cl)Cl>[C:9]([O:8][C@H:7]1[C@@H:12]([O:13][C:14](=[O:16])[CH3:15])[C@@H:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:18][C@@H:5]([S:41][C:40]2[CH:35]=[CH:36][C:37]([CH3:47])=[CH:38][CH:39]=2)[C@@H:6]1[N:24]1[C:25](=[O:34])[C:26]2=[CH:33][CH:32]=[CH:31][CH:30]=[C:27]2[C:28]1=[O:29])(=[O:11])[CH3:10]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 87122-ThiocresolHCID 127757051,3,4,6-Tetra-o-acetyl-2-deoxy-2-phthalimido-beta-d-galactopyranose

生成物 1

HCID 69963625p-Methylphenyl 3,4,6tri-o-acetyl-2-deoxy-2-phthalimido-1-thio-beta-d-galactopyranoside収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranose (Nilsson, U. et al. Carbohydr. Res. 1990, 208, 260) (1.7 g, 3.56 mmol) in CH2Cl2 (20 mL) was treated with thiocresol (663 mg, 5.34 mmol) and BF3.Et2O (1.5 mL) by the procedure described in the preparation of 1. After workup, the crude product was crystallized from Et2O. to gave the title compound 11 (1.62 g, 83%): m.p. 141-142° C.; [α]D22 +45.4° (c, 0.5, CHCl3); 1H-NMR (400 MHz, CDCl3), δ 1.97 (s, 3H), 2.05 (s, 3H), 2.08 (s, 3H), 2.31 (s, 3H), 4.09-4.24 (m, 3H), 4.62 (t, 1H, J=10.8 Hz), 5.49 (d, 1H, J=3.2 Hz), 5.64 (d, 1H, J=10.8 Hz), 5.80 (dd, 1H, J=10.8, 3.2 Hz), 7.07 (d, 2H, J=8.1 Hz), 7.32 (d, 2H, J=8.1 Hz), 7.76-7.80 (m, 4H); 13C-NMR (400 MHz, CDCl3) δ 20.52, 20.69, 21.14, 50.11, 61.63, 66.85, 68.81, 74.48, 84.35, 123.65, 129.62, 133.21, 134.40, 162.01, 163.10, 167.16, 167.90, 171.22; HRMS for C27H27NO9SCs (M+Cs) calcd 674.0461, found 674.0435.

後処理

  1. customdescribed in the preparation of 1
  2. customAfter workup, the crude product was crystallized from Et2O

出典と根拠

ORDレコード
ord-25092e847ffe46bbbcc6fb6798eda6c6
出典データセット
uspto-grants-2003_03
特許番号
US06538117B1

反応ノート

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