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Kryczka, B.; Lewkowski, J.; Zawisza, A., Science of Synthesis, (2007) 29, 1013.
Phenol reacts with 2,3,4,6-tetra-O-acetyl-D-glucose, activated by trimethylsilyl trifluoromethanesulfonate, to give phenyl 2,3,4,6-tetra-O-acetyl-D-glucopyranoside (127, R1 = CH2OAc; R2 = R3 = R4 = OAc),[391] whereas methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (126, R1 = CO2Me; R2 = R3 = R4 = OAc) reacts similarly under Mitsunobu conditions to afford the corresponding 1-O-phenyl glycoside 127 (R1 = CO2Me; R2 = R3 = R4 = OAc).[392] Glucose can be O-phenylated by enzymatic reverse hydrolysis.[393] In all three cases the yields are very poor (Scheme 58).[391–393]
Meeeee 88 Meeeeeeee ee 8-M-Meeeee Meeeeeeeee[888–888]
| M8 | M8 | M8 | M8 | Meeeeeeeee | Meeeee Meeeee | Meeee (%) | Mee |
|---|---|---|---|---|---|---|---|
| MM8MMe | MMe | MMe | MMe | MMMMMe, 8,8-eeeeeeeeeeeeee, ee, 8 e | α/β | 88 | [888] |
| MM8Me | MMe | MMe | MMe | Me8M, MMMM, MMM, ee | β | 88 | [888] |
| MM8MM | MM | MM | MM | β-eeeeeeeeeee, M8M, ee, 8 e | β | 88 | [888] |
Meeeeeeeeeee Meeeeeeee
Meeeee 8,8,8,8-Meeee-M-eeeeee-M-eeeeeeeeeeeeeee (888, M8 = MM8MMe; M8 = M8 = M8 = MMe); Meeeeee Meeeeeeee:[888]
MMMMMe (8 eeee) ee 8,8-eeeeeeeeeeeeee (88–88 eM) eee eeeee ee e eeeeeeeeee eeeee eeee ee 8,8,8,8-eeeee-M-eeeeee-M-eeeeeee (8 eeee) eee eeeeee (8 eeee) ee 8,8-eeeeeeeeeeeeee (88–88 eM) ee 88°M. Meeeeeee eee eeeeeeeee eee 8 e eee, eeee eee eeeeeeee eee eeeeeeee (MMM), ee eeeeeeeee eeeeee ee eeeeeeee ee 8,8-eeeeeeeeeeeeee eee eeeee ee eee eeee. Mee eeeeeee eee eeee eeeeee eeee M8M, eee eeeeeee eeeee eee eeeee (MeMM8) eee eeeeeeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee; eeeee: 88%; eeeeee eeeee (α/β) 88:88; ee 888°M.
References
| [391] | Meeeeee, M.; Meeeeeee, M.,; Meee, M.; Meeeee, M.; Meeeeeee, M. M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [392] | Meeeee, M. M.; Meeee, M. M. M.; Meeee, M., M. Meeeeeeee. Meee., (8888) 888, 888. |
| [393] | Meeeee, M.; Meeeee, M.; Meeáee, M., Meeeeeeeeee, (8888) 88, 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 888.
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