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, CH 2 Ph), 4.11-4.06 (m, 3H, HB-6, HB-6' and HA-6), pp.4-7
, GlcNAc-H6', GlcNAc-H6, pp.4-21
, CH, CB-5 or CC-3), 73.2, 73.2, 72
, 1H, H4), 3.85 (t, J 6',5 = J 6',6' = 10, Hz, 1H, H6'), 2.45 (d, J OH,3 = 7.5 Hz, 1H, OH), p.3630
, CH 2 Ph), 69.5 (CH, chromatography on silica gel (heptane/EtOAc 9:1 to 6:4) to afford pure product 249 (876 mg, 59 %, white amorphous solid) and pure product, CH, C2), 80.1 (CH, C4), p.250
, 85-3.82 (m, 2H, H6 and H6'), 3.79 (t, Hz, 1H, H4), 2.43 (d, J OH,2 = 9.0 Hz, 1H, OH), 2.35 (s, 3H, ArCH 3 ), pp.4-19, 2000.
, 82 (dd, J A6',A6 = 11.0 Hz and J A6',A5 = 3.5 Hz, 1H, HA-6'), 3.82-3.74 (m, 2H, HA-4 and HB-2), 3.58 (ddd, J B5,B4 = 10, Hz, J B5,B6 = 4.5 Hz and J B5,B6' = 2.5 Hz, 1H, HB-5), 2.86 (brs, 1H, OH), 2.37 (s, 3H, ArCH 3 ), 2.02 (s, 3H, OCOCH 3 ), 2.01 (s, 3H, OCOCH 3 ), p.8130
, TTBP (65 mg, 0.258 mmol, 4 eq Fe(OTf) 3 ·6.2DMSO (10 mg, 0.010 mmol, 15 mol-%)
, 59-3.54 (m, 2H, HB-5 and HC-5), 2.37 (s, 3H, ArCH 3 ), 2.03 (s, 9H, 3×OCOCH 3 ), 2.01 (s, 3H, OCOCH 3 ), pp.89-92
, 34 (s, 3H, ArCH 3 ), 2.02 (s, 3H, OCOCH 3 ), 2.00 (s, 3H, OCOCH 3 ), 1.95 (s, 3H, pp.52-55
, HC-6, HD-2 and HD'-2, HE-6 and HE'-6), 4.15-3, pp.4-26
, HD-3 and HD'-3, HD-4 and HD'-4, HD-6' and HD'-6', HD-7'and HD'-7', HD-9, HE-5 and HE'-5, HF-5 and HF (m, 1.4H, HD-5 and HD'-5, HD'-9, HF-2 and HF, ), 2.05 (s, 1.5H, COCH 3 ), 2.04 (s, 1.5H, COCH 3 ), 2.03 (s, 1.5H, COCH 3 ), 2.03 (s, 1.5H, COCH 3 ), pp.8278-8281
, CE-2 and CE
, 0 Hz, 1H, CH 2 Ph), 4.58 (d, J = 12, Hz, 1H, CH 2 Ph), 4.55 (d, J = 12.0 Hz, 1H, CH 2 Ph), 4.54 (d, J = 11.0 Hz, 1H, CH 2 Ph 1H, CH 2 Ph), 4.39 (s, 1H, H1), 4.05 (dt, J 7 Hz, 1H, H7), 3.91 (d, J, pp.4-64
, 74 (dd, J 6',6 = 10.5 Hz and J 6, pp.65-68
, 8 = 7.5 Hz and J 7',8' = 4.5 Hz, 1H, and H8'), pp.54-57
, 54-3.43 (m, 3H, HA-5, HA-7', HC-5, HD-3, HD-9 and HD-9'), 3.34-3.28 (m, 1H, HA-9 and HA-9, 1H, HD-5 and HF-2), 3.16 (dt, J B2), 2.06 (s, 1.5H, COCH 3 ), 2.05 (s, 1.5H, COCH 3 ), 2.05 (s, 1.5H, COCH 3 ), 2.04 (s, 1.5H, COCH 3 ), 2.04 (s, 1.5H, COCH 3 ), pp.72-75
, 80 (t, J 6,5 = J 6,6' = 10, Hz, 1H, H6'), 2.96 (d, J OH,2 = 1.0 Hz, 1H, OH), 2.31 (s, 3H, ArCH 3 ), 1.27 (s, 9H, ArC(CH 3 ) 3 ), 1.09 (s, 9H, Si(Ph) 2 C(CH 3 ) 3 )
, 75 (m, 2H, H6 and H6'), 3.74 (dd, 5 Hz, 1H, H2), 2.23 (s, 3H, ArCH 3 ), 1.25 (s, 9H, ArC(CH 3 ) 3 ), 1.13 (s, 9H, Si(Ph) 2 C(CH 3 ) 3 ), pp.98-378
, TTBP (100 mg, 0.402 mmol
, HB-4), 4.93 (s, 1H, C4 = 10.0 Hz, 1H, HC-3), 4.74 (d, J = 10.5 Hz, 1H, CH 2 Ph), pp.4-97, 2005.
, 4.63 (d, J 7',7 = 12.5 Hz, 1H, pp.4-57
, HC-1), 4.34-4.31 (m, 2H, HA-2 and HD-6), C2 = 8.0 Hz, pp.4-15
, 72 (m, 4H, HD-5, HB-5 and CH 2TEG, pp.8177-369
, 08 (s, 3H, COCH 3 ), 2.08 (s, 3H, COCH 3 ), 2.04 (s, 3H, COCH 3 ), 2.04 (s, 3H, C6' = 2.5 Hz COCH 3 ), 2.02 (s, 3H, COCH 3 ), 2.01 (s, 3H, COCH 3 ), 2.00 (s, 3H, COCH 3 ), 1.99 (s, 3H, COCH 3 ), 1.99 (s, 3H, COCH 3 ), 1.92 (s, 3H, COCH 3 ), pp.14-38958
, 60 (m, 13H, HA-4, HA-5, HD-2, HB-2, GlcNAc-H3, 2×GlcNAc-H6' and 3×CH 2TEG ), 3.57-3.56 (m, 2H, HC-2 and GlcNAc-H3), 3.54-3.49 (m, 4H, HA-6', GlcNAc-H3 and CH 2TEG, -4 and HD-5), 2.04 (s, 3H, COCH 3 ), 2.03 (s, 3H, COCH 3 ), pp.69-337
, 3 (CH, CB-5, CC-5 or CD-5), 78.1 (CH, CB-5, CC-5 or CD-5), 78.1 (CH, CB-5, CC-5 or CD-5), CH, CD-3 or CB-3 or CC-3)
, 49 mmol, 3.5 eq.) in dry CH 2 Cl 2 (4.5 mL), at ? 78 °C under argon, was added dropwise along the sides of the flask a solution of 3- chloroperoxybenzoic acid 75 % (197 mg, 0.85 mmol, 1.2 eq.) in CH 2 Cl 2 (5.5 mL) 268 After stirring at ? 78 °C for 1 hour and then at ? 20 °C overnight, the reaction mixture was diluted with CH 2 Cl 2 (20 mL) and successively washed with saturated aqueous Na 2 S 2 O 3 (20 mL), saturated aqueous NaHCO 3 (20 mL) and brine (60 mL). The organic layer was separated and 268 According to the procedure of: G, 71 mmol, 1 eq.) and NaHCO 3 (209 mg, pp.298-4727, 2008.
, 52 (s, 3H, ArCH 3 )
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