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

HRID 1862751노트

반응식

HRID 1862751 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-25092e847ffe46bbbcc6fb6798eda6c6
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06538117B1

반응 노트

불러오는 중…