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29.15.1.1.3 Method 3: Synthesis from 1-O-Acetyl Glycosides

DOI: 10.1055/sos-SD-029-00907

Kryczka, B.; Lewkowski, J.; Zawisza, A., Science of Synthesis, (2007) 29, 975.

Although early studies focused on the glycosidation of 1-O-acetyl sugars with phenol using 4-toluenesulfonic acid or zinc(II) chloride, other promoters are often now used for the formation of 1-O-methyl glycosides ‌18‌ from 1-O-acetylated monosaccharides ‌17‌. These reagents include boron trifluoride–diethyl ether complex, trimethylsilyl trifluoromethanesulfonate, tin(IV) chloride, and iron(III) chloride (‌Scheme 6‌).[‌12‌,‌13‌,‌25‌–‌33‌]

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

‌Meeeeeeeeee 8‌

Meeee Meeeee M8 M8 M8 M8 Meeeeeeeee Meeeee Meeeee Meeee (%) Mee
β-M-eeeee MM8MMe MMe MMe MMMMMM8 MM8•MMe8, ee β 88 [‌88‌,‌88‌]
β-M-eeeee MM8MMe MMe MMe MMe MeMe8, 8-Å ­eeeeeeeee eeeeee β/α 88/88 [‌88‌]
α-M-eeeee MM8MMe MMe MMe M MMMMMe, 8-Å eeeeeeeee eeeeee, 8 e α 88 [‌88‌]
β-M-eeeee MM8MMe MMe MMe MMMM8MM8MM=MM8 MMMMMe, ee, 8 e α 88 [‌88‌,‌88‌]
β-M-eeeee MM8MMMe-Me MMMe-Me MMMe-Me MMMe-Me MMM, MeMeM8, 88.8 e β 88 [‌88‌]
M-eeeeeee MM8MMe MMe MMe MMe MeMe8, ee, 8 eee α 88 [‌88‌]
β-M-eeeee MM8MMe MMe MMe M Meeee-88M(M+), 88–88°M, 88 e –e 88 [‌88‌]
M-eeeee MM8MMe MMe MMe MMMe MeMe, eeee, 88 e α 88 [‌88‌]

e Mee eeeeeeee.

Meeeeeeeeeee Meeeeeeee

Meeeee 8,8,8-Mee-M-eeeeee-8-eeeee-8-(eeeeeeeeeeeeeeeeee)-β-M-eeeeeeeeeeeeeee (β-M-eeeee-‌88‌, M8 = MM8MMe; M8 = M8 = MMe; M8 = MMMMMM8); Meeeeee Meeeeeeee:[‌88‌]

MM8•MMe8 (8.8 eM, 88.88 eeee) eee eeeee ee eee 8-M-eeeeee eeeeeeeee M-eeeee-‌88‌ (M8 = MM8MMe; M8 = M8 = MMe; M8 = MMMMMM8; 8 e, 88.88 eeee) eee MeMM (8.88 eM, 88.88 eeee) ee eeeee MM8Me8 (88 eM), eee eee eeeeeee eee eeeeeee eeeeeeeee ee ee. Mee eeeeeeeee eee eee eeeeeee eee eeeeeee eeee MeMMe (888 eM) eee eeeeee eeee eee. ee MeMMM8 (8 × 888 eM). Mee eeeeeee eeeee eee eeeeeeeee, eeeee (Me8MM8), eee eeeeeeeeeeee ee eeeee e eeeeeeee eeeeee eeeee; eeeee: 8.8 e (88%); Me 8.88 (eeeeee eee, eeeeeee/MeMMe 8:8).

References

[12] Meeeeeeeee, M.; Meeeee, M.; Meeeeeee, M., Mee. M. Meee., (8888) 88, 8888.
[13] Meeeee, M.; Meeeee, M.; Meeeeeeeee, M.; Meeeeeee, M., Meeeeeeee. Mee., (8888) 888, 88.
[25] Mee, M.; Meeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888.
[26] Meeeeeee, M.; Meeeeee, M.; Meeeeeeee, M., M. Meeeeeeee. Meee., (8888) 88, 888.
[27] Meeeeeeeeeeeee, M.; Meeeeeeeee, M.; Meeeeeeeee, M.; Meeeeeeeeeee, M.; Meeeeeeee, M., Meeeee M. Meee., Meee. M, (8888) 88, 888.
[28] Meeeee, M.; Meeeeeeeee, M.; Meeeeeeeee, M., M. Meeeeeeee. Meee., (8888) 88, 8888.
[29] Meeeeeeee, M.; Meeeeeeee, M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888.
[30] Meeeeeeee, M.; Meeeeeeee, M.; Meee, M., Meee. Meee., (8888), 8888.
[31] Meeeeeeeee, M. M.; Meee, M., Meee. Meeeee. (Meeeeeeee), (8888), 8888.
[32] Meee, M. M.; Meeeee, M., Meeeeeeee. Mee., (8888) 888, 888.
[33] Meee, M.; Meeeee-Meeee, M., Meeeeeeee. Mee., (8888) 888, 888.

Meeeeee Meeeeeeeeee

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

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