, , vol.174
, MALDI-TOFMS m?z calcd for C137H133NO37
, , p.50
,
, 2C, 2 × OCH3(C6 B,E )), 59.98 (2C, 2 × OCH3(C2 B,E )), vol.60
,
,
,
, , pp.3-82
, 27 mmol) and imidazole (54 mg, 3.0 eq., 0.80 mmol) in dry PhMe (7.2 mL) and dry CH3CN (5.5 mL) was added dry triethylamine (0.05 mL, 1.2 eq., 0.32 mmol) and 4 Å molecular sieve. The reaction mixture was stirred at 90 ?C for 1d and at 110 ?C for 3d. The solvent was evaporated under vacuum. The residue was subjected to silica gel column (eluent : DCM / MeOH = 15 :1, then 10 :1 and 7 :1) to get the crude ?-CD Me -NHC-OMs, which was passed through LH-20 column to remove the free imidazole. The pure ?-CD Me -NHC-OMs was dissolved in water
, Note: ?-CD Me -NHC-OMs can dissolve in PhMe
, 400 MHz, CD3CN, 300K): ? 2.80 (m, 1H, J1 = 6.65 Hz, J2 = 10.57 Hz, 1 × H6a B ), 3.05 (m, 4H, 1 × H2 E , 1 × OCH3(C6 B )), 3.08 (m, 1H, 1 × H2 F ), 3.11 (m, 3H, 1 × H2 B , 1 × H2 C , 1 ×H6b B ), 3.14 (m, 1H, 1 × H2 G ), 3.16 (m, 1H, 1 × H6a E ), 3.22
, 3.59 (m, 1H, 1 × H6a F ), 3.61 (s, 3H, 1 × OCH3(C3 G )), 3.62 (m, 1H, 1 × H5 B ), 3.64 (m, 1H, 1 × H6a G ), 3.68 (m, 1H, 1 × H5 C ), 3.69 (m, 1H, 1 × H6b F ), 3.70 (s, 3H, 1 × OCH3(C3 C )), 3.78 (m, 1H, 1 × H4 C ), 3.79 (m, 1H, 1 × H3 C ), 3.80 (m, 1H, 1 × H5 F ), 3.88 (m, 2H, 1 × H6b G , 1 × H6b C )
, To a solution of ?-CD Me -NHC-Cl 3-82b (50 mg, 0.034 mmol) in dry and degassed CH3CN (2 mL) was added K2CO3(23 mg, 0.17 mmol) and AuSMe2Cl (25 mg
After stirred at 50 ?C overnight, the reaction mixture was diluted by DCM and subjected to silica gel chromatography, vol.10 ,
, 400 MHz, CD3CN, 300K): ? 2.74 (dd, 1H, J1 = 4.00 Hz, J2 = 10.87 Hz, 1 × H6a F ), 2.89 (dd, 1H, J1 = 1.54 Hz, J2 = 11.04 Hz, 1 × H6b F )
28 (s, 3H, 1 × OCH3(C6 E )), 3.30 (m, 1H, 1 × H6b B ), 3.32 (s, 3H, 1 × OCH3(C3 G )), 3.33 (s, 3H, 1 × OCH3(C6 C )), 3.40 (m, 4H, 1 × H5 B , 1 × OCH3(C2 B )), 3.41 (s, 3H, 1 × OCH3(C2 D )), 3.42 (s, 3H, 1 × OCH3(C2 F ), 3H, 1 × OCH3(C6 B )), 3.24 (m, 1H, 1 × H2 A ), 3.25 (m, 1H, 1 × H3 B ), vol.3, p.1 ,
, s, 3H, 1 × OCH3(C3 C )), 3.62 (m, 1H, 1 × H6a G ), 3.63 (m, 1H, 1 × H3 F ), 3.66 (m, 1H, 1 × H5 C ), 3.68 (m, 2H, 1 × H5 G , 1 × H6a C ), 3.69 (m, 1H, 1 × H5 E ), 3.70 (m, 1H, 1 × H4 G ), 3.75 (m, 4H, 1 × H6a D , 1 × OCH3(C3 G )), 3.76
,
,
, ×OCH3(C6 F )), 59.31 (1C, 1 ×OCH3(C6 C )), vol.59, p.1
, ×OCH3(C3 G )), 61.97 (1C, 1 ×OCH3(C3 D )), 61.98 (1C, 1 ×OCH3(C3 C )), 62.01 (1C, 1 ×OCH3(C3 B )), 62.11 (1C, 1 ×OCH3(C3 F )), vol.70, pp.71-84
, 47 (1C, 1 × C2 B ), 82.52 (1C, 1 × C2 C ), 31 (1C, 1 × C3 E ), 82.32 (1C, 1 × C4 C ), 82.42 (2C, 1 × C3 C , 1 × C3 F ), vol.82
, 99.16 (1C, 1 × C1 B ), 99.99 (1C, 1 × C1 E ), vol.123
, 13 C NMR (150 MHz, CD3CN, 300K): ? 53.59 (1C, 1 × C6 D ), 55.39 (1C, 1 × C6 A ), 57.98 (1C, 1 × OCH3(C2 E )), 58.09 (1C, 1 × OCH3(C2 C )), 58.17 (1C, 1 × OCH3(C2 D )), 58.72 (1C, 1 × OCH3(C2 F )), 58.77 (1C, 1 × OCH3(C2 A )), 58.99 (1C, 1 × OCH3(C6 C )), 59.14 (2C, 1 × OCH3(C6 B ), 1 × OCH3(C6 F )), 59.20 (1C, 1 × OCH3(C6 E )), 59.32 (1C, 1 × OCH3(C6 G )), 59.72 (1C, 1 × OCH3(C2 G )), p.61
, 12 (1C, 1 × C2 B ), 82.18 (1C, 1 × C3 F ), vol.82, p.63
, mmol) was dissolved in CD3CN (0.4 mL, from vial) into a NMR tube
3-105 downshifted from 4.80 ppm to 5.30 ppm of 3-106. MS spectrum was shown as followed ,
, H NMR (400MHz, CDCl3, 300K): ? 3.00 (dd, 2H, J1 = 6.49 Hz, J2 = 10.49 Hz, 2 × H6a B,E )
,
, , vol.2
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