Table 1.

Synthesis of octyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (4) by reaction of 3 with 1-octanol.^a

Entry	Reaction conditions	Time [h]	Yield (%)b	Ratio of 4 to 5c	Reference
1	Ag2CO3, CaSO4	10	33	4.4	43
2	Ag2CO3, CaSO4, I2	10	26	9.0	43
3	Ag2CO3, 4 Å MS	10	8	1.7	43
4	I2, DDQ, 4 Å MS	3	36	16	10
5	AgOTf, TMU, 4 Å MS	4	23	2.8	11
6	AgOTf, TMU	4	17	3.2	11

^aReactions in anhydrous dichloromethane (1 mL/0.1 g) were performed at ambient temperature using the following amounts of the reagents: Ag₂CO₃ (1.05 mol equiv), CaSO₄ (same weight as Ag₂CO₃), 4 Å MS (0.1 g/mL), AgOTf (2.2 mol equiv), and TMU (3 mol equiv). With exception of entry 4 all reactions were performed in the dark.

^bIsolated yield.

^cDetermined by gas chromatography and based on relative peak area.

MS = molecular sieves; DDQ = 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; TMU = 1,1,3,3-tetramethyl urea.