Skip to main content
. Author manuscript; available in PMC: 2013 Jul 1.
Published in final edited form as: Carbohydr Res. 2012 Apr 21;355:19–27. doi: 10.1016/j.carres.2012.04.010

Table 1.

Generation of partially and fully deprotected GlcN(α1→4)Glc sulfoforms

graphic file with name nihms372199u1.jpg
sulfoforma 9 (yield from 1, ops)b 2 (yield from 9)c
graphic file with name nihms372199t1.jpg
a 		52%, 6 ops (a, b, d, e, h, k) 87%
graphic file with name nihms372199t2.jpg
b 		39%, 6 ops (a, g, d, e, c, k) 83%
graphic file with name nihms372199t3.jpg
c 		36%, 7 ops (a, e, h, c, i, j, k) 84%
graphic file with name nihms372199t4.jpg
d 		48%, 6 ops (a, b, g, d, f, k) 97%
graphic file with name nihms372199t5.jpg
e 		42%, 6 ops (a, b, i, f, h, k) 98%
graphic file with name nihms372199t6.jpg
f 		40%, 6 ops (a, g, i, f, c, k) 97%
graphic file with name nihms372199t7.jpg
g 		54%, 6 ops (a, b, g, i, f, k) 99%
a

9a–g: R=Bn, R′=Cbz; 2a–g: R, R′=H. All products are isolated as sodium salts.

b

Isolated yield after HPLC purification. Each step was conducted at rt unless otherwise noted. Reagents and conditions: (a) CAN (3 equiv), 90% aq CH3CN, 0 °C, 10 h; (b) TBAF (6 equiv), THF, 6 h; (c) TBAF (8–10 equiv), 1:1 THF:DMF, 24–40 h; (d) 1:5 AcSH:Py, 48 h; (e) SO3·Me3N (20–30 equiv), DMF, 55 °C, 12 h; (f) SO3·Py (20–30 equiv), 1:5 Et3N:Py, 70 °C, microwave, 1 h; (g) MgBr2·Et2O (10 equiv.), CH3NO2 (20 equiv), Et2O, 10 h; (h) MgBr2·Et2O (10 equiv.), 1:2 CH3NO2:Et2O, 24–48 h; (i) HS(CH2)3SH (35 equiv), Et3N (35 equiv), MeOH, 24 h; (j) SO3·Py (10 equiv), 5:1 H2O:DMF, pH 9.5, 8 h; (k) Na+ ion exchange chromatography.

c

10% Pd(OH)2, H2 (1 atm), 1:1 MeOH:H2O, 20 h.