Optimization conditions for the synthesis of S-glycosides^a.

Entry	F− sources	Solvent	Time/h	T/°C	Yield (%)
1	CsF	CH3CN	2.0	25	70(64b)
2	AgF	CH3CN	2.0	25	51
3	KF	CH3CN	2.0	25	42
4	ZnF2	CH3CN	2.0	25	35
5	TBAF·3H2O	CH3CN	2.0	25	63
6	TBAF(THF)	CH3CN	2.0	25	67
7	TBAF·(tBuOH) 4	CH 3 CN	2.0	25	86
8	TBAF·(tBuOH)4	DCM	2.0	25	78
9	TBAF·(tBuOH)4	THF	2.0	25	40
10	TBAF·(tBuOH)4	Toluene	2.0	25	33
11	TBAF·(tBuOH)4	MeOH	2.0	25	37
12	TBAF·(tBuOH)4	DMSO	2.0	25	26
13	TBAF·(tBuOH)4	DMF	2.0	25	30
14	TBAF·(tBuOH)4	CH3CN	2.0	40	85
15	TBAF·(tBuOH)4	CH3CN	2.0	60	60
16	TBAF·(tBuOH)4	CH3CN	3.0	25	83c
17	TBAF·(tBuOH)4	CH3CN	4.0	25	82

^aStandard conditions: 1a (0.1 mmol, 1.0 equiv.), 2a (0.11 mmol, 1.1 equiv.), TBAF·(tBuOH)₄ (0.2 mmol, 2.0 equiv.), CH₃CN (1.5 mL) as solvent, r.t., 2 h.

^b1a (0.1 mmol, 1.0 equiv.), 2a (0.1 mmol, 1.0 equiv.), F⁻ source (0.2 mmol, 2.0 equiv.), CH₃CN (1.5 mL).

^c1a (0.1 mmol, 1.0 equiv.), 2a (0.11 mmol, 1.1 equiv.), TBAF·(tBuOH)₄ (0.3 mmol, 3.0 equiv.), CH₃CN (1.5 mL) as solvent, r.t., 2 h.