Table 1.

Evaluation of stereoselectivity using donors with no 2-O acyl groups

$\text{Donor}\left(1\text{equiv}\right)+\mathrm{AgOTf}\underset{\text{then acceptor}\left(0.9\text{equiv}\right),-60--20°\mathrm{C}}{\overset{p-\mathrm{TolSCI}\left(1\text{equiv}\right),-60°\mathrm{C}}{\to }}\text{Glycoside product}$
Entry	Donor	Acceptor	AgOTf	Reaction condition	Pdt	Yield % (α:β)
1	1	2	3	a	3	67 (1.1:1)
2	1	2	10	a	3	66 (1:1.5)
3	1	2	1.1	a	3	69 (6:1)
4	1	2	1.1	a*	3	55 (10:1)
5	1	2	3	b	3	92 (1:1.8)
6	1	2	1.1	b	3	90 (1:8)
7	1	4	1.1	a	5	80 (5.7:1)
8	1	4	1.1	b	5	71 (1:1.7)
9	1	6	1.1	a	7	86 (2:1)
10	1	6	1.1	b	7	79 (1:9.4)
11	1	8	1.1	a	9	69 (α only)
12	10	2	1.1	a	11	69 (6:1)
13	10	2	1.1	b	11	56 (1:1.2)
14	12	4	1.1	a	13	70 (α only)
15	12	4	1.1	b	13	90 (1:1.2)
16	12	6	1.1	a	14	65 (2:1)
17	12	6	1.1	b	14	92 (β only)
18	12	6	1.1	b**	14	90 (β only)
19	12	8	1.1	a	15	74 (α only
20	16	4	1.1	a	17	61 (α only)
21	16	6	1.1	a	18	58 (2:1)
22	16	6	1.1	b	18	71 (1:3)

a) Reaction was performed in diethyl ether (donor concentration was 50 mM). b) Reaction was performed in dichloromethane (donor concentration was 50 mM).

^*Donor concentration is 5 mM.

^**Toluene (5% of final volume) was added to the reaction to dissolve AgOTf.