2,6-Lutidine → HCID 69929968, compound

HRID 2120976Notes

Reaction equation

HRID 2120976 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:15]([CH2:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[O:14][C@@H:11]([O:12][CH3:13])[C@@H:10]1[OH:35])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.[Si:44](OS(C(F)(F)F)(=O)=O)([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45]>C(Cl)Cl>[CH2:1]([O:8][C@H:9]1[C@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:15]([CH2:25][O:26][CH2:27][C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)[O:14][C@@H:11]([O:12][CH3:13])[C@@H:10]1[O:35][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 22956578HCID 22956578, compound

Product 1

HCID 69929968HCID 69929968, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 3,4-di-O-benzyl-6-O-(4-chlorobenzyl)-β-D-glucopyranoside (0.258 g, 0.517 mmol) was dissolved in 3 mL CH2Cl2. 2,6-lutidine (240 μL, 2.06 mmol) and tert-butyldimethylsilyltrifluoromethane sulfonate (0.284 mL, 1.24 mmol) were added and the reaction mixture was stirred at room temperature for 30 min. The solution was filtered through silica, eluted with EtOAc and concentrated. Purification by flash column chromatography on silica gel (10% EtOAc/Hexanes) gave 283 mg (89%) of 22 as a colorless oil. [α]24D: −9.2° (c 2.01, CH2Cl2); IR (thin film) 2928, 2855, 1492, 1069 cm−1; 1H-NMR (CDCl3) δ 7.41-7.29 (m, 12H), 7.16-7.13 (m, 2H), 4.97 (d, J=11.3 Hz, 1H), 4.90 (d, J=11.3 Hz, 1H), 4.82 (d, J=11.0 Hz, 1H), 4.61 (d, J=12.5 Hz, 1H), 4.56-4.53 (m, 2H), 4.17 (d, J=7.3 Hz, 1H), 3.78-3.76 (m, 1H), 3.71 (dd, J=4.6, 10.7 Hz, 1H), 3.63-3.53 (m, 6H), 0.95 (s, 9H), 0.17 (s, 3H), 0.13 (s, 3H), 13C-NMR (CDCl3) δ 138.8, 138.1, 136.8, 133.5, 129.2, 128.6, 128.5, 128.4, 128.3, 128.0, 127.9, 127.5, 104.9, 86.0, 78.3, 75.8, 75.4, 75.1, 74.9, 72.8, 69.1, 57.9, 26.1, 18.4, −4.1, −4.2; FAB MS m/z (M+Na)+: calcd 635.2572, obsd 635.2574.

Workup

  1. filtrationThe solution was filtered through silica
  2. washeluted with EtOAc
  3. concentrationconcentrated
  4. customPurification by flash column chromatography on silica gel (10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-8720bab0bfb5461f9fb5192d9664a672
Source dataset
uspto-grants-2004_02
Patent number
US06693178B2

Reaction notes

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