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

HRID 1862751Notes

Reaction equation

HRID 1862751 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-25092e847ffe46bbbcc6fb6798eda6c6
Source dataset
uspto-grants-2003_03
Patent number
US06538117B1

Reaction notes

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