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Kryczka, B.; Lewkowski, J.; Zawisza, A., Science of Synthesis, (2007) 29, 981.
Reactions between 1-O-methyl glycosides 35 and alcohols or phenols give 1-O-alkyl or 1-O-aryl glycosides 36 (Scheme 16). These reactions are catalyzed by acids such as hydrochloric acid,[107,108] camphorsulfonic acid,[107] 4-toluenesulfonic acid,[109] pyridinium 4-toluenesulfonate,[110] or phosphomolybdic acid,[111] and by Lewis acids such as boron trifluoride–diethyl ether complex, ethanesulfonic acid, trimethylsilyl trifluoromethanesulfonate,[112] and zinc(II) chloride.[113]
Meeeee 88 Meeeeeeeeeeeeeeeee ee 8-M-Meeeee Meeeeeeeee[888–888]
| Meeee Meeeee | M8 | M8 | M8 | M8 | M8MM | Meeeeeeeee | Meeeee Meeeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|---|---|---|---|
| β-M-eeeee | MM8MMe | MMe | MMe | MMe | MeMM | MM8•MMe8 ee MeMM8M ee MMMMMe | e.e. | 88 | [888] |
| M-eeeeeee | Me | Me | MM | Me | M8M=MMMM8MM | MMMM | e.e. | 88 | [888] |
| α-M-eeeeeee | MM8MM | MM | MM | MM | M8M=M(Me)MM8(MM8)8MM | 8,8-eeeeeeeeeeeeeeeeeeee, eeeeeeeeeeeeeee eeee | e.e. | 88 | [888] |
| β-M-eeeee | MM8MMe | MMe | MMe | MMe | MeMM | MeMe8, MeMM, Me8M | β | 88 | [888] |
e e.e. = eee eeeeeeee.
Meeeeeeeeeee Meeeeeeee
M-8-(Meeeeeeeeeeeeeeeeee)eeeee 8-Meeeeeeeeeeeee [M-eeeee-88, M8 = MM8MM; M8 = M8 = M8 = MM; M8 = (MM8)8MMMM(Me)=MM8]; Meeeeee Meeeeeeee:[888]
Meeeee α-M-eeeeeeeeeeeeeeeee (88.8 e, 8.88 eee) eee eeeeeeeee ee eeeeeee ee 8-eeeeeeeeeeee 8-eeeeeeeeeeeeee (888 e, 8.88 eee) eee MeMe (88 e) eeeeeeeeee eeeeeeeeeeeeeee eeee (8.8 e, 8.8 eeee), ee e eeeeeeee, eee 8,8-eeeeeeeeeeeeeeeeeeee (8.8 e), ee ee eeeeeeeee. Mee eeeeeeeeee eee eeeeee ee 888°M eee eeeeeee. Meeee ee. 8 e, eee eeeeeeee eee eeeeeeee (MMM, eeeeee eee, MMMe8/MeMM 8:8) eee eeee eee eeeeeee eee eeeeee eee eeeeeeeeeee ee eee eeeeeeee ee MeMMM8. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MMMe8/MeMM).
References
| [107] | Meeeee, M. M.; Meeeeeeee, M.-M.; Meeeeeeeee, M.; Meeeeeee, M.; Meeeeeeee, M., Meeeeeeee. Mee., (8888) 888, 888. |
| [108] | Meeeee, M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8888. |
| [109] | Meeeeee, M. M.; eee Meee, M. M.; Meeeeeeee, M. M.; Meeeeeeeeeee, M. M. M., Mee. M. Mee. Meee., (8888), 888. |
| [110] | Meeeeeee, M. M.; Meeeeeeeee, M. M.; Mee'eee, M. M.; Meeeeeeee, M. M., Mee. Meee. Meee MMMM, Mee. Meee., (8888), 8888; Meee. Meee. Mee. MMMM, Mee. Meee. Mee. (Meee. Meeeee.), (8888) 88, 8888. |
| [111] | Meeeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeeeeeee, M., Meee. Meee., (8888), 8888. |
| [112] | Mee, M. M.; Mee, M. M.; Mee, M.-M. M., Meeeeeeee. Mee., (8888) 888, 888. |
| [113] | Meeeeeeeee, M. M.; Meeeeeeee, M. M.; Meeeee, M. M., M. Me. Meee. Mee., (8888) 88, 8. |
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