151992-75-5

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 151992-73-3 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl chloride 
• 152141-82-7 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl nitrate 
• 166516-68-3 ethyl 2-azido-2-deoxy-1-thio-β-D-glucopyranoside 
• 129519-27-3 2-((6S,7R,8aS)-8-benzyloxy-6-ethylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-isoindole-1,3-dione 
• 75-03-6 ethyl iodide 
• 151992-74-4 1-S-acetyl-2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 

Downstream Products

• 151992-81-3 Methyl O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-(1->4)-O-(2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(tert-butyl 2,3-di-O-benzyl-β-D-glucopyranosid)uronate 
• 151992-77-7 ethyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-1-thio-β-D-glucopyranoside 
• 200938-37-0 Phosphoric acid (1R,2R,3S,4R,5R,6R)-2-((2R,3R,4R,5S,6R)-3-azido-4-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-3,4,5,6-tetrahydroxy-cyclohexyl ester dibenzyl ester 
• 129210-15-7 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate 
• 371788-63-5 C₅₇H₆₅N₃O₁₀ 
• 201015-92-1 O-(4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl) trichloroacetimidate 
• 439684-08-9 ethyl 2-azido-4-O-benzoyl-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 439684-01-2 ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside S-oxide 
• 439684-07-8 ethyl 4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 200938-30-3 ethyl 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 120312-00-7 4-O-allyl-2-azido-3,6-di-O-benzyl-2-desoxy-D-glucopyranose 
• 120312-13-2 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride 

Relevant academic research and scientific papers

Efficient routes to glucosamine-myo-inositol derivatives, key building blocks in the synthesis of glycosylphosphatidylinositol anchor substances

Short synthetic routes to protected derivatives of 2-amino-2-deoxy-α-D-glucopyranosyl-(1→6)-D-myo-inositol are described. Various 2-azido-2-deoxy-glucosyl donors were synthesized, starting from D-glucal or glucosamine hydrochloride. Derivatives of 1,2- and 2,3- D-myo-inositol-camphanylidene acetals were prepared to function as glycosyl acceptors. The subsequent glycosylations produced useful building blocks for the synthesis of GPI-anchor substances.

Synthesis of part of a proposed insulin second messenger glycosylinositol phosphate and the inner core of glycosylphosphatidylinositol anchors

Synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate, an inner core structure found in various glycosylphosphatidylinositols, and the corresponding 1,2-cyclic phosphate, proposed as part of an insulin second messenger glycosylinositol phosphate, is described. Chirality in the inositol part of the molecule was achieved by the use of a known D-camphor acetal intermediate. The glycosylation used 4-O-allyl-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride as glycosyl donor. The allyl group can be chemoselectively removed, opening a route to oligosaccharides bound to the 4-position of the glucosamine unit. The phosphorylation was accomplished by the phosphoramidate procedure.

Synthesis of the methyl glycosides of a tri- and a tetra-saccharide related to heparin and heparan sulphate

The methyl glycoside of a tetrasaccharide isolated from heparin, methyl O-(α-L-idopyranosyluronic acid)-(1 → 4)-O-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1 → 4)-O-(β-D-glucopyranosyluronic acid)-(1 → 3)-O-β-D-galactopyranoside disodium salt and a trisaccharide derivative thereof, methyl O-(α-L-idopyranosyluronic acid)-(1 → 4)-O-(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1 → 4)-O-β-D-glucopyranosyluronic acid disodium salt, were synthesized using a block-type strategy. A suitable protected disaccharide block of iduronic acid and glucosamine (IdoA-GlcN) was used as a key intermediate for the syntheses and was glycosidated with a protected galactose derivative and a disaccharide block of glucuronic acid and galactose (GlcA-Gal) to give tri- and tetra-saccharide derivatives, respectively. Deprotection gave the target compounds. The methyl glycoside of a tetrasaccharide isolated from heparin, disodium salt and a trisaccharide derivative thereof, were synthesized using a block-type strategy. A suitable protected disaccharide block of iduronic acid and glucosamine (IdoA-GlcN) was used as a key intermediate for the syntheses and was glycosidated with a protected galactose derivative and a disaccharide block of glucuronic acid and galactose (GlcA-Gal) to give tri-and tetra-saccharide derivatives, respectively. Deprotection gave the target compounds.