Skip to main content
. 2022 Mar 17;13(14):4122–4130. doi: 10.1039/d2sc00222a

Disaccharide formation using unprotected 2-acetamido sugars as donors, and unprotected glycosides as acceptorsa.

Entry Donor Acceptor Product Isolated yield of (1→6) linked disaccharide (%) Regioselectivity/total combined yield
1 GlcNAc 2a graphic file with name d2sc00222a-u8.jpg graphic file with name d2sc00222a-u9.jpg 49 (1→6) only
2 GlcNAc 2a graphic file with name d2sc00222a-u10.jpg graphic file with name d2sc00222a-u11.jpg 46 (1→6) only
3 GlcNAc 2a graphic file with name d2sc00222a-u12.jpg graphic file with name d2sc00222a-u13.jpg 25 3 regioisomers/50%
4 GlcNAc 2a graphic file with name d2sc00222a-u14.jpg graphic file with name d2sc00222a-u15.jpg 40e (1→6) onlye
5 GlcNAc 2a graphic file with name d2sc00222a-u16.jpg graphic file with name d2sc00222a-u17.jpg 36 3 regioisomers/48%
6 GlcNAc 2a graphic file with name d2sc00222a-u18.jpg graphic file with name d2sc00222a-u19.jpg 33 3 regioisomers/55%
7 GlcNAc 2a graphic file with name d2sc00222a-u20.jpg graphic file with name d2sc00222a-u21.jpg 32a 2 regioisomers/46%a
44b (1→6) onlyb
8 GlcNAc 2a graphic file with name d2sc00222a-u22.jpg graphic file with name d2sc00222a-u23.jpg 39e (1→6) onlye
9 GlcNAc 2a graphic file with name d2sc00222a-u24.jpg graphic file with name d2sc00222a-u25.jpg 31a 3 regioisomers/62%a
37d 3 regioisomers/54%d
10 GlcNAc 2a graphic file with name d2sc00222a-u26.jpg graphic file with name d2sc00222a-u27.jpg 39a 3 regioisomers/68%a
26b 3 regioisomers/52%b
11 GlcNAc 2a graphic file with name d2sc00222a-u28.jpg graphic file with name d2sc00222a-u29.jpg 45 (1→6) < 1% of any other regioisomer
12 GlcNAc 2a graphic file with name d2sc00222a-u30.jpg graphic file with name d2sc00222a-u31.jpg 34a 3 regioisomers/47%a
39b 3 regioisomer/58%b
13 GlcNAc 2a graphic file with name d2sc00222a-u32.jpg graphic file with name d2sc00222a-u33.jpg 18 3 regioisomers/51%
14 GalNAc 2b graphic file with name d2sc00222a-u34.jpg graphic file with name d2sc00222a-u35.jpg 40 (1→6) only
15 GalNAc 2b graphic file with name d2sc00222a-u36.jpg graphic file with name d2sc00222a-u37.jpg 26a 2 regioisomers/40%a
30c (1→6) onlyc
16 ManNAc 2c graphic file with name d2sc00222a-u38.jpg graphic file with name d2sc00222a-u39.jpg 15 (1→6)/trace amount of another regioisomer
a

Reaction conditions: (i) DMC 1, Et3N, H2O, 0 °C, 1 h, then freeze-dry; acceptor (3a–i or 5d), MeCN/DMF (10 : 1), 4 Å powdered molecular sieves, TsOH, rt, 3 h.

b

Reaction performed at 0 °C.

c

Reaction performed at −10 °C.

d

Reaction performed at −16 °C for 24 h.

e

Reaction performed in DMF as solvent.