W0 2011/000721 A1 I||||||||||||||||||||||||||||||||||||||||||||||||||||||||| - Questel
W0 2011/000721 A1 I||||||||||||||||||||||||||||||||||||||||||||||||||||||||| - Questel
W0 2011/000721 A1 I||||||||||||||||||||||||||||||||||||||||||||||||||||||||| - Questel
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28.30 (C3 D ). HRMS (ESI) : Calculated for [C 24 H 39 N 3 O 16 Na 1 + = 648.22225,<br />
experimental = 648.22127 (error 1.5 ppm).<br />
5) Synthesis of the α(1,2) α(1,6)pseudomannotriose 10<br />
To a solution of the compound 2b (27.4mg, 0.044 mmol, 1eq) in MeOH (2.2<br />
ml.) a catalytic amount of Pd on carbon was added. The suspension was put<br />
under hydrogen atmosphere and stirred at room temperature monitoring by<br />
TLC (CHCI 3 :MeOH:H 2 O [75:25:3]) After one hour the reaction was finished, the<br />
reaction mixture was filtered over a celite pad and the solvent was evaporated<br />
at reduced pressure, obtaining 26 mg of pure product 10 (99%).<br />
[af D =+64.01 (c:1.95, CH 3 OH)<br />
1 H-NMR (400 MHz, CD3 OD) δ (ppm): 4.95 (d, 1H , H 1M , Ji- 2 = 1 Hz), 4.79 (d,<br />
1H, H 1 M Jv-2- = 1.6 Hz), 4.07 (bs, 1H, D 2 ), 3.90-3.81 (m, 4 H 1 H 2M , H 2M , H 6B M ,<br />
H 6 BM), 3.80-3.74 (m, 3H, D 1 , H 78 , H 6 AM-). 3.74-3.54 (m, H, H 6AM , H 3M , H 3M ., H 4 M',<br />
H 5M , H 5M , H 4M ), 3.66 (s, 6H, OCH 3 ), 3.54-3.46 (m, 1H, H 7A ), 3.00 (dt, 1H, D 5 ,<br />
= 12 Hz, 4 Hz), 2.90-2.78 (m, 1H, D 4 ), 2.84 (t, 2H, H 8 , J 7 - 8<br />
= 5.2 Hz), 2.16 (app d , 1H, D 6ax , J gem = 13.6 Hz), 2.04 (app d , 1H, D 3ax , J gem =<br />
14.0 Hz), 1.83 (t, 1H, D 3βq ), 1.75 (t, 1H, D 6eq ). 13 C-NMR (100 MHz, C D 3 OD) δ<br />
(ppm): 177.25, 177.02 (COOCH 3 ), 101 .87 (C1 M ), 100.37 (C1 M ), 76.06 (C1 D ),<br />
75.52 (C4M), 74.08 (C4 M ), 72.66, 72.57, 72.52 (C2 M , C2 M ., C3 M , C3 M ), 7 1.98
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