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

HRID 1862751Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862751
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-25092e847ffe46bbbcc6fb6798eda6c6
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06538117B1

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