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29.15.1.1.1 Method 1: Synthesis from Free Sugars

DOI: 10.1055/sos-SD-029-00907

Kryczka, B.; Lewkowski, J.; Zawisza, A., Science of Synthesis, (2007) 29, 972.

The direct formation of a glycosidic bond from a sugar with a free anomeric hydroxy group can be a highly efficient process and methods based on the original Fischer–Helferich protocol using an acid catalyst are useful for obtaining simple methyl glycosides ‌10‌ when methanol is the alcohol. However, in some cases the reactions can also be catalyzed by bases, metal salts, or resins (‌Scheme 2‌).[‌3‌–‌10‌]

‌Meeeee 8‌ Meeeeeeee ee 8-M-Meeeee Meeeeeeeee eeee Meee Meeeee[‌8‌–‌88‌]

‌Meeeeeeeeee 8‌

Meeee ­Meeeee M8 M8 M8 M8 Meeeeeeeee Meeeee Meeeee Meeee (%) Mee
M-eeeee MM8MM MM MM MMMM8MM8MMe8 MMe, eeee, 8.8 e α 88 [‌8‌]
M-eeee Me MM MM MM MMe, 88 e β 88 [‌8‌]
M-eeee Me MM MM MM 8.8 M MMe β 88 [‌8‌]
M-eeeee MM8MM MM MM MMMe MeMe, eeee α 888 [‌8‌,‌8‌]
M-eeeee MM8MM MM MM MM MeMe, eeeeeeeee α 888 [‌8‌]
M-eeeee MM8MM MM MM MM Meeee 88M-M8 α 88 [‌8‌]
M-eeeee Me MM MM MM Meeeeeeee MM-888 (M+) –e 88 [‌88‌]

e Mee eeeeeeee.

Meeeeeeeeeee Meeeeeeee

Meeeee α-M-Meeeeeeeeeeeeee (α-M-eeeee-‌88‌, M8 = MM8MM; M8 = M8 = M8 = MM); Meeeeee Meeeeeeee:[‌8‌]

M eeee ee α-eeeeeee (888 ee, 8.88 eeee) ee eeeee MeMM (8 eM) eee eeeee eeee e eeeeee-eeeeeeee eeeee (Meeee 88M-M8; 888 ee) eeee eee eeee eeeeeeeeee eeeeee ee eeee eeee M8M, 8 M MMe, M8M, eee MeMM. Mee eeeeeee eee eeeeeeee eeeeeeeee eee eeee eeeeee ee ee. Mee eeeee eee eeeeeee ee eeeeeeeeee eee eee eeeeeeee eee eeeeeeeeeeee ee eeee eee eeeee eeeeeeee ee e eeeeeee eee; eeeee: 888 ee (88%).

References

[3] Meeeee, M. M.; Meeeeeee, M., Meee. Meeeee. (Meeeeeeee), (8888), 888.
[4] Me, M.; Meeeeeee, M. M.; Meeee, M. M.; Me, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888.
[5] Meeee, M.; Meee, M.; Meeeeeee, M.; Meee, M. M.; Meeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888.
[6] Me, M.; Meeee, M.; Meee, M., Meeeeeeee. Mee., (8888) 888, 88.
[7] Meeeeeee, M. M. M.; Meeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeee, M. M. M.; Meee, M. M.; Meeee, M. M.; Meeee, M. M., Mee. Meeeee. Meee., (8888) 8, 8888.
[8] Müeeeee, M.; Meeeeeeeee, M.; Meeeeeeeeeäeee, M., Meeee. Meeeee., (8888) 88, 8888.
[9] Meeee, M.; Meeeee, M.; Meeeeeeeeee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888.
[10] Meeeeee, M.; Meeeee, M.; Meeeee, M.; Meeeeeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888.

Meeeeee Meeeeeeeeee

  • 8.Meeeee-Meee, (8888) M 88e8, 888.
  • 8.Meeeee-Meee, (8888) M 88e8, 888.
  • 8.Meeeee-Meee, (8888) M 88e, 8888.

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