, J. Name, vol.00, pp.1-3, 2012.

H. C27?, , 0128.

H. D26?, 00 (5s, 6H, CH 3Ac26 , CH 3Ac27 , CH 3Ac28 , CH 3NHAc26 , CH 3NHAc27 , CH 3NHAc28 ), NHCO, vol.2, issue.9, pp.29-30, 2002.

*. C28?, J. , and H. , C-1 C26?* , 1 J C,H = 171.0 Hz), vol.101

J. and H. , , vol.100

*. E28?, C. -1-e28?, *. , and J. , 5 Hz), 99.8 (C-1 E27?* , C-1 E27?* , 1 J C,H = 172.6 Hz), 99.2 (C-1 C26?

C. D25?, J. -1-d28?, and H. , , vol.92

J. D28?, 6 Hz), 63.8, 63.2, 63.0 (C-6 D? , C-6 D? , C-6 E? , C-6 E? ), vol.58

, ESI + ): m/z 594.1964 (calcd for C 22 H 37 NO 16 Na, HRMS, p.594, 2010.

R. , Journal Name ARTICLE This journal is © The Royal Society of Chemistry, J. Name, vol.00, pp.1-3, 2012.

3. , N. H. , and H. Ar, 88 (m, 1H, CH=CH 2 ), 5.28 (m, 1H, J trans = 17.2 Hz, J gem = 1.7 Hz, CH=CH 2 ), 5.21 (m, 1H, J cis = 10.4 Hz, Tol/EtOAc 6:4 to 3:7) gave trisaccharide 42 (200 mg, 99%) as a white foam. The diol had 1 H NMR (CDCl 3 ) ? 7.38-7.13 (m, vol.5

H. Hz, 1. Bn-;-d-po, J. Hz, and H. Bn, , vol.2, p.3

, 67 (d po , 1H, J 5,6a = 1.9 Hz, J 6a,6b = 10.5 Hz, H-6a E ), 3.62 (dd, 1H, J 1,2 = 3.6 Hz, vol.3

. Hz, 13 C NMR (CDCl 3 ) ? 169.9 (NHCO), 138.4-137.1 (6C, C IVAr ), vol.133

J. Hz-;-c-1-c-,-1 and H. ,

, 79.1 (C-2 E ), vol.77

, 67.8 (C-6 E ), vol.46, p.22

H. ,

|. J. Name, This journal is © The Royal Society of Chemistry, vol.00, pp.1-3, 2012.

H. Hz and 3. -6b-e-)-;-s, 72 (s, 3H, CH 3NHAc ), 1.29 (d, 3H, J 5,6 = 6.2 Hz, H-6 C ), 0.91 (bs, 9H, CH 3tBuSi ), 0.14 (bs, 3H, SiCH 3 ), 0.05 (bs, 3H, SiCH 3 ), vol.2

;. Hz, J. , and H. , , vol.95

, 82.1 (C-3 E ), vol.81

. , 69.4 (C All ), vol.68

. , CH 3NHAc ), 21.0 (CH 3Ac ), 25.8 (3C, CH 3tBuSi ), vol.22

, HRMS (ESI + ): m/z 1266.5991 (calcd for C 73 H 92 NO 16 Si [M+H] + m/z 1266.6185)

, 42 (dd, 1H, J 1,2 = 1.8 Hz, J 2,3 = 3.2 Hz, H-2 B ), 5.31 (m, 1H, J trans = 17.3 Hz, J gem = 1.7 Hz, CH=CH 2 ), + m/z 1288.6005). The coupling product 33 had: 1 H NMR (CDCl 3 ) ? 7.36-7.11 (m, 41H, 40H Ar , NH), 5.95 (m, 1H, CH=CH 2 ), vol.5

H. Hz, 1. Bn-;-d-o, H. Bn-;-d-o, 1. , and H. Bn,

D. and H. -3-b,

1. Hz-;-bd-po and 4. Lev, 12 (s, 3H, CH 3Lev ), 1.74 (s, 3H, CH 3NHAc ), 1.29 (d o , 3H, J 5,6 = 6.0 Hz, H-6 C ), 1.28 (d o , 3H, 6b = 10.7 Hz, H-6b E ), vol.2, pp.129-130

;. Hz, J. , and H. , , vol.95

, HRMS (ESI + ): m/z 1598.6995 (calcd for C 92 H 105 NO 22 Na, vol.7026, p.1598

3. and H. Bn, Following addition of DCM (80 mL) and water (35 mL), the two layers were separated and the aq. one was extracted twice with DCM. The combined organic extracts were washed with 5% aq. citric acid (35 mL), and brine (100 mL), then dried over anhyd. Na 2 SO 4 and concentrated to dryness. The residue was purified by flash chromatography (Tol/EtOAc 8:2 to 0:1) to give alcohol 45 (0.86 g, 96%) as a white foam, To a solution of tetrasaccharide 33 (960 mg, 0.61 mmol) in anhyd. pyridine (30 mL) stirred at 0°C under an Ar atmosphere were added dropwise AcOH (10 mL) and hydrazine monohydrate (215 µL, 4.42 mmol, vol.5, pp.3-46

. , C-2 E ), vol.78, p.75

. , 69.3 (C All ), 69.1 (C-2 B ), 68.8 (C-5 C ), 70.6 (C-4 D ), vol.68

, HRMS (ESI + ): m/z 1500.6599 (calcd for C 87 H 99 NO 20 Na, vol.6658, p.1500

, To a stirred solution of tetrasaccharide 45 (299 mg, vol.46

. Etoh, The suspension was stirred under an H 2 atmosphere for a day at rt. After this time, MS analysis of revealed a molecular weight corresponding to that of the target tetrasaccharide and the absence of any molecular weight corresponding to the benzylated intermediates. The reaction mixture was filtered over a pad of Celite. Evaporation of the volatiles, freeze-drying and purification of the residue by RPMPLC (0-50% linear gradient of 80% aq. MeCN over 60 min at a flow rate of 20 mL?min-1 ) gave tetrasaccharide 46 (140 mg, 90%) as a white powder following repeated freeze-drying, were added Pd/C (299 mg) and 1M aq, vol.9, p.3

H. Hz and E. -6b, , vol.2, p.3

, 50 (dt, 1H, J = 6.6 Hz, J = 12.8 Hz, OCH 2Pr, vol.3, p.5

3. Psex, 2. , and J. =. , 27 (d, 3H, J 5,6 = 6.2 Hz, H-6 C ), 1.23 (d, 3H, J 5,6 = 6.2 Hz, H-6 B ), 0.85 (t, 3H, J = 7.4 Hz, CH 3Pr ), = 170.7 Hz), vol.1, pp.1-3, 2012.

, C-2 E ), 72.7 (2C, C-2 B , C-3 B ), vol.74, pp.74-75

H. , HRMS (ESI + ): m/z 1541, vol.760

R. , , vol.8

, To a stirred solution of slightly contaminated tetrasaccharide 46 (82 mg, 108 µmol), issued from RP-HPLC purification, MeOH (8 mL), was added methanolic sodium methoxide to reach pH 10, p.25

, MS analysis revealed the presence of the target tetrasaccharide and the absence of any starting 46. The reaction was neutralized by addition of Dowex H + resin, and the suspension was filtered over a 0.2 µm filter. Evaporation of the volatiles, freeze-drying and purification of the residue by RP-MPLC (0-50% linear gradient of 80% aq. MeCN over 60 min at a flow rate of 20 mL?min-1 ) gave tetrasaccharide 47 (47 mg, 60%) as a white powder following repeated freeze-drying. The fully deprotected tetrasaccharide 47, The solution was stirred at rt for 15 h. After this time

. Hz,

. Hz, , pp.3-94

. Hz,

. Hz,

C. , H. -5, B. Och-2pr, H. -3, C. et al.,

. Hz,

3. Hz-;-s, 2. Psex, and J. =. , 28 (d, 3H, J 5,6 = 6.2 Hz, H-6 C ), 1.25 (d, 3H, J 5,6 = 6.2 Hz, H-6 B ), 0.85 (t, 3H, J = 7.5 Hz, CH 3Pr ) ; 13 C NMR (D 2 O) ? 176.5 (NHCO), = 170.0 Hz), vol.1, p.71

H. , , vol.3134, p.718

H. ,

R. , R t = 9, vol.9

, Alcohol 45 (350 mg, 0.24 mmol) and trichloroacetimidate 32 (210 mg, 0.36 mmol, 1.5 equiv.) were dissolved in anhyd. DCE (7 mL), and activated 4Å MS (0.31 g) was added. The suspension was stirred for 25 min at rt, then TfOH (7 µL, 79 µmol, 0.3 equiv.) was added. After stirring for 5 h at rt, a TLC control (Tol/EtOAc 6:4) showed the disappearance of the acceptor (Rf 0.29) and the presence of a major less polar product (Rf 0.60). The mixture was neutralized by addition of Et 3 N, and the suspension was filtered over a pad of Celite. Volatiles were removed under reduced pressure and the crude material was purified by flash chromatography (Tol/EtOAc 8:2 to 0:1) to give a 3:7 mixture of the hydrolyzed donor 48 and of the desired pentasaccharide 49 as a white foam. The coupling product 49 had 1 H NMR (CDCl 3 ) ? 7

4. , H. Bn-;-m, 3. , H. -1, D. et al., 1H, H-1 E ), 4.80 (d po , 1H, J = 11.2 Hz, H Bn

2. Hz-;-m, H. -4, A. , H. -6b-e-;-m, and 4. Lev, 17 (s, 3H, CH 3Lev ), 2.14 (s, 3H, CH 3Ac ), 1.74 (bs, 3H, CH 3NHAc ), 1.19 (d, 3H, J 5,6 = 6.2 Hz, H-6 B ), 1.13 (d, 3H, vol.2, pp.138-144

J. Hz-;-c-1-a-,-1 and H. , , vol.170

;. Hz, J. , and H. , , vol.95

, 79.0 (C-2 E ), 77.6 (C-3 A ), 77.5 (C-4 E ), vol.79, p.75

, ESI + ): m/z 1924.8542 (calcd for C 112 H 127 NO 26 Na, HRMS, vol.8544, p.1924

, HRMS (ESI + ): m/z 1902, vol.8735, p.1903

, HRMS (ESI + ): m/z 973.9128

, To a solution of pentasaccharide 49 (400 mg, 0.21 mmol) in anhyd. pyridine (11 mL) stirred at rt under an atmosphere of Ar, were added dropwise AcOH (7 mL) and hydrazine monohydrate (70 µL, 1.44 mmol, 7.0 equiv.). The reaction mixture was stirred at rt for 3 h. Following addition of DCM (35 mL) and water (35 mL), the two layers were separated and the aq. one was extracted twice with DCM (2 x 35 mL). The combined organic extracts were washed with 5% aq. citric acid (75 mL), brine (75 mL), then dried over anhyd. Na 2 SO 4 and concentrated to dryness. The residue was purified by flash chromatography (Tol/EtOAc 8:2 to 0:1) to give product of delevulination 50 (0.27 g, 63% over 2 steps) as a white foam, Alcohol, vol.50

|. J. Name, This journal is © The Royal Society of Chemistry, vol.00, pp.1-3, 2012.

1. Po, 2 = 1.5 Hz, H-1 B ), 4.88 (bs po , 2H, H Bn ), 4.87 (d po , 1H, J = 10.7 Hz, H Bn ), 4.85 (d po , 1H, J = 11.1 Hz, H Bn ), vol.1, pp.3-89
URL : https://hal.archives-ouvertes.fr/hal-00265614

C. and H. , , p.5

, H-6 C ), 1.09 (d, 3H, J 5,6 = 6.2 Hz, H-6 A ), vol.169, pp.138-145

. Hz, 100.6 (C-1 A , 1 J C,H = 171.1 Hz), vol.97

;. Hz, J. , and H. , , vol.95

, HRMS (ESI + ): m/z 1826.7903 (calcd for C 107 H 119 NO 24 Na [M+Na] + m/z 1826.8176), HRMS (ESI + ): m/z 924.9005 (calcd for C 107 H 119 NO 24 Na 2 [M+2Na] 2+ m/z 924.9037), HRMS (ESI + ): m/z 921, vol.8867

, To a stirred solution of pentasaccharide 50 (322 mg, 178 µmol) in 90% aq. EtOH (13.5 mL), were added Pd/C (300 mg) and 1M aq. HCl (33.5 µL). The suspension was stirred under H 2 atmosphere for a day at rt. After this time, MS analysis of the reaction mixture revealed a molecular weight of corresponding to that of the target pentasaccharide. The reaction mixture was filtered over a pad of Celite. Evaporation of the volatiles, freeze-drying and purification of the residue by RP-MPLC (0-50% linear gradient of 80% aq. MeCN over 60 min at a flow rate of 20 mL?min-1 ) gave pentasaccharide 51 (149 mg, 92%) as a white powder following repeated freeze-drying

. Hz, , pp.5-14

, 41 (pt po , 1H, J 3,4 = J 4,5 = 9.6 Hz, H-4 A ), 2.15 (s, 3H, CH 3Ac ), 1.99 (s, 3H, CH 3NHAc ), 1.53 (psex, 2H, J = 6.9 Hz, CH 2Pr ), 1.30 (d, 3H, J 5,6 = 6.2 Hz, H-6 C ), 1.27 (d, 3H, J 5,6 = 6.1 Hz, H-6 B ), 1.24 (d, 3H, J 5,6 = 6.3 Hz, H-6 A ), 0.85 (t, 3H, J = 7.4 Hz, CH 3Pr ), OCH 2Pr ), 3.43 (pt o , 2H, J 3,4 = J 4,5 = 9.8 Hz, H-4 B , H-4 E ), vol.3, pp.3-57

, 72.1 (C-5 B ), vol.71

, HRMS (ESI + ): m/z 906.3813 (calcd for C 37 H 63 NO 24 [M+H] + m/z 906.3818), HRMS (ESI + ): m/z 928.3572 (calcd for C 37 H 63 NO 24 Na [M+Na] + m/z 928.3638), HRMS (ESI + ), vol.7412, p.1833

R. ,

, To a stirred solution of pentasaccharide 51 (91 mg

. Meoh, After this time, MS analysis of the reaction mixture revealed a molecular weight of corresponding to that of the target tetrasaccharide. The reaction solution was neutralized by addition of Dowex H + resin, and the suspension was filtered over a 0.2 µm filter. Evaporation of the volatiles, freeze-drying and purification of the residue by RP-MPLC (0-50% linear gradient of 80% aq. MeCN over 60 min at a flow rate of 20 mL?min-1 ) gave pentasaccharide 52 (73 mg, 85%) as a white powder following repeated freeze-drying. The fully deprotected, mL), was added methanolic sodium methoxide (25% w/w, 25 µL), vol.52

. Hz, , pp.3-89

. Hz, 64 (dq po , 1H, H-5 A ), 3.60 (pt po , 1H, J 2,3 = J 3,4 = 9.6 Hz, H-3 E ), 3.54 (ddd po , 1H, J 5,6a = 2.1 Hz, J 5,6b = 4.6 Hz, J 4,5 = 10.0 Hz, H-5 E ), 3.50 (dd po , 1H, J 2,3 = 9.8 Hz, H2 E ), 3.48 (pt o , 1H, J 3,4 = J 4,5 = 9.8 Hz, H-4 C ), 3.44 (dt, 1H, J = 6.6 Hz, J = 9.6 Hz, OCH 2Pr, = 170.2 Hz), vol.3, pp.3-36

, HRMS (ESI + ): m/z 451.6599 (calcd for C 35 H 61 NO 23 Na [M+H+Na] 2+ m/z 451.6675), HRMS (ESI + ): m/z, vol.864

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