“Standardized intermediates” for oligosaccharide synthesis: convenient preparation of 2-amino-2-deoxy-d-glucose derivatives and their conversion into the d-galactose analogues

Synthesis of Fucosyl Saccharides under Neutral Conditions in Solutions of Lithium Perchlorate in Dichloromethane

“…Encouraged by these results, we treated 5 with the glucosamine-derived glycosyl acceptor 8, which carries a less reactive secondary hydroxyl group. Compound 8 was built up from 13 [11] by acetylation of the 3-OH group ( 314; see the Experimental Section) and subsequent regioselective opening of the benzylidene acetal present in the acetate 14 in high yield (Scheme 3).…”

“…To a solution of 13 [11] (224 mg, 0.5 mmol) in pyridine (4 mL) acetic anhydride (0.5 mL) was added. After stirring for 18 h at room temperature, the mixture was poured into ice water and the mixture was extracted twice with chloroform (10 mL).…”

Efficient and practical syntheses of three pentasaccharides core structures corresponding to N -glycans

“…and NaOAc (4 equiv.) in 90% aqueous acetic acid, 9 followed by anomeric Schmidt activation 10 with trichloroactonitrile furnished trisaccharide donor 14 in 83% yield (2 steps). Convergently, coupling of donor 9 with acceptor 4 was accomplished in 40 min using TMSOTf (0.1 equiv.)…”

Synthesis of Anomeric Sulfimides and Their Use as a New Family of Glycosyl Donors

“…Ethyl 3,4,6‐Tri‐ O ‐acetyl‐2‐deoxy‐2‐phthalimido‐ S ‐( N ‐tosylimino)‐1‐thio‐β‐ D ‐glucopyranoside (7): Preparation from ethyl 3,4,6‐tri‐ O ‐acetyl‐2‐deoxy‐2‐phthalimido‐1‐thio‐β‐ D ‐glucopyranoside22 (160 mg, 0.334 mmol) according to Procedure A and purification by column chromatography (petroleum ether/ethyl acetate, 2:8) gave amorphous 7 (141 mg, yield 65%) in the form of one epimer. [α] D = −46 ( c = 1.0, CHCl 3 ).…”