18464-08-9

Upstream product

• 92052-38-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 
• 14227-66-8 acetobromocellobiose 
• 252653-17-1 8-[2-(benzyloxy)ethyl]naphthalene-1-ethanol 

Downstream Products

• 106256-89-7 (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 
• 92052-38-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide 
• 92052-38-5 O-<2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α,β-D-glucopyranosyl>trichloroacetimidate 
• 109922-77-2 Cyclohexanecarboxylic acid (2S,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester 
• 109922-78-3 Cyclohexanecarboxylic acid (2R,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester 
• 30854-62-7 lactosyl azide 
• 467465-69-6 Boc-Glu(Bn)-NH-[Lac(OAc)7] 
• 467465-70-9 Boc-Lys(Cbz)-NH-[Lac(OAc)7] 
• 160720-83-2 (2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-α/β-D-glucopyranosyl trichloroacetimidate 
• 196305-18-7 Thexyldimethylsilyl (2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzoyl-β-D-glucopyranoside 
• 160720-73-0 8-methoxycarbonyloctyl-2,3,6,2',6'-penta-O-benzoyl-β-D-lactoside 
• 191034-33-0 8-methoxycarbonyloctyl-2,3,6,2',6'-penta-O-benzoyl-3',4'-O-isopropylidene-β-D-lactoside 
• 196305-22-3 thexyldimethylsilyl (6-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-6-O-benzoyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Oligosaccharide analogues of polysaccharides. Part 19. Synthesis of 2- (naphthalen-1-yl)ethyl cellooligoglycosides and [(naphthalene-1,8- diyl)di(ethane-2,1-diyl)] bis[cellooligoglycosides]

Glucosyl, cellobiosyl, cellotriosyl, cellotetraosyl, and cellooctaosyl residues were attached to naphthalene-1,8-diethanol (3) with the goal of preparing mimics of cellulose I. Among the templates that were considered, 1,8-diethynylnaphthalene (1) led to unstable products, and glycosidation of naphthalene-1,8-dimethanol (2) gave orthoesters that could not be rearranged to glycosides (Scheme 1). The conformation of 3 in the crystal and of its dimethyl ether 14 in solution was studied by X-ray analysis and force-field calculation (Figs. 1-3). Rotation around the Ar-CH2 and CH2-CH2 bonds of 14 is only weakly hindered and the O···O distance of crystalline 3 (6.01 A) corresponds to the mean distance of the parallel chains of cellulose I(β). The acetylated glycosyl bromides 18 and 19 were prepared by a new convergent synthesis (Scheme 2). Glycosylation of 3 by the glycosyl bromides 15-19 under established conditions of the Koenigs-Knorr reaction proved problematic, particularly on account of an acetyl transfer blocking one of the hydroxyethyl groups. Basic zinc carbonate, however, promoted glycosylation of 12 and 3 by the glycosyl bromides 15-19 and did not lead to transacetylation (Scheme 3). The mono- to tetrasaccharides 32-35 and 42-45 were isolated in yields of 5682%, and the octasaccharides 36 and 46 in 32 and 16%, respectively. The mono- and disaccharides 32, 33, 42, and 43 were deacetylated with NaOMe in MeOH. Aqueous NaOH was used for the tri-, tetra-, and octasaccharides 34-36 and 44-46, as their partially deacetylated derivatives proved insoluble in MeOH. The fully deprotected saccharides 37-41 and 47-50 were isolated in over 90%, while the yield of the dioctaoside 51 was lower on account of its poor water solubility.

Studies on the synthesis of two tetrasaccharides and the reactivity difference between them

Studies on the reactivity of two synthetic tetrasaccharides as glycosyl acceptors showed that condensation of the methyl α-glycoside with a disaccharide donor afforded a hexasaccharide, but condensation of the methyl β-glycoside with the disaccharide did not yield the corresponding hexasaccharide under the same conditions. A combination of theoretical results and 2D NMR indicated that the reactivity difference between the methyl α-glycoside and the methyl β-glycoside was determined mainly by steric effects.