173398-22-6

Upstream product

• 190779-52-3 ethyl-3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-D-glucopyranoside 
• 29741-67-1 1,3,4,6-tetra-O-acetyl-2-O-benzyl-β-D-glucopyranoside 
• 173314-28-8 phenyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-α-D-glucopyranoside 

Downstream Products

• 181026-00-6 6-((2S,3R,4S,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxy)-hexanoic acid methyl ester 
• 29741-69-3 3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide 
• 127066-75-5 methyl 3,4,6-tri-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 181026-02-8 6-[(2S,3R,4S,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-((3aR,4R,6R,7R,7aS)-4-acetoxymethyl-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester 
• 189144-74-9 C₅₆H₇₄O₂₅ 
• 189144-71-6 C₅₁H₇₀O₂₆ 
• 189144-72-7 C₄₈H₆₆O₂₆ 
• 189144-69-2 6-[(2S,3R,4S,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester 
• 189144-79-4 5-(methoxycarbonyl)pentyl O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->2)-O-(3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-acetyl-α-D-glucopyranoside 
• 127066-72-2 Acetic acid (2R,3R,4S,5R)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-thiocyanato-tetrahydro-pyran-4-yl ester 
• 173314-32-4 decyl 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Koenigs–Knorr Glycosylation Reaction Catalyzed by Trimethylsilyl Trifluoromethanesulfonate

The discovery that traditional silver(I)-oxide-promoted glycosidations of glycosyl bromides (Koenigs–Knorr reaction) can be greatly accelerated in the presence of catalytic trimethylsilyl trifluoromethanesulfonate (TMSOTf) is reported. The reaction conditions are very mild that allowed for maintaining a practically neutral pH and, at the same time, providing high rates and excellent glycosylation yields. In addition, unusual reactivity trends among a series of differentially protected glycosyl bromides were documented. In particular, benzoylated α-bromides were much more reactive than their benzylated counterparts under these conditions.

HEPARANASE INHIBITORS FOR TREATMENT OF DIABETES

Anti-heparanase compounds for the treatment of diabetes are described. The anti-heparanase compounds are high affinity, synthetic glycopolymers that result in minimal anticoagulant activity. Stereoselective fluorinated forms of these compounds are also pr

HEPARANASE INHIBITORS AND THEIR USE AS ANTI-CANCER COMPOUNDS

Anti-heparanase compounds for the treatment of cancer are described. The anti-heparanase compounds are high affinity, synthetic glycopolymers that result in minimal anticoagulant activity. Stereoselective fluorinated forms of these compounds are also prov

Phenanthroline-Catalyzed Stereoretentive Glycosylations

Carbohydrates are essential moieties of many bioactive molecules in nature. However, efforts to elucidate their modes of action are often impeded by limitations in synthetic access to well-defined oligosaccharides. Most of the current methods rely on the

Synthesis of kojidextrins and their protein conjugates. Incidence of steric mismatch in oligosaccharide synthesis

Kojidextrins are biologically important oligosaccharides that are involved in many physiological processes including protein glycosylation and bacterial growth. As part of our project to explore the role kojidextrins may play in bacterial pathogenesis, here we report synthetic routes to kojibiose (54), -triose (58), -tetraose (64), and -pentaose (69) equipped with α-linked (hydrazinocarbonyl)pentyl aglycon, using linear and convergent strategies. In the search for a rapid convergent strategy for the construction of extended kojidextrins, four kojibiose donors (1-4) were synthesized that contain acyl- and ether-type protecting groups in various ratios. These were tested to probe the influence of diverse protecting group assemblies on their glycosyl donor ability. Attempted condensation of these donors with kojitriose and -tetraose acceptors failed to give the desired products apparently because of steric mismatch between the donor and the acceptor moieties. A one-pot procedure was developed for the covalent attachment of the synthetic saccharides through their hydrazido group to human serum albumin (HSA) using Tietze's squarate method to give neoglycoproteins containing up to 28 saccharide units per HSA.

Synthesis of a pentasaccharide fragmant of Polysaccharide II of Mycobacterium tuberculosis

Stereocontrolled, stepwise synthesis of decyl glycosides of α-(1 -->2)-linked di- to pentaglucosides (1-5) is described; these constitute fragments of Polysaccharide II of Mycobacterium tuberculosis.Phenyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-?-D-glucopyranoside (7) was used as the single key intermediate, obtained from 1,3,4,6-tetra-O-acetyl-2-O-benzyl-β-D-glucopyranose (6) and PhSSiMe3.Halogenolysis of 7 afforded the isolated β bromide (10) and β chloride (13).Solvolysis of 10 with decanol without heavy metal salts gave decyl 3,4,6-tri-O-acetyl-2-O-benzyl-α-D-glucopyranoside (14) in a highly stereoselective reaction, in high yield.Subsequent, iterative hydrogenolytic removal of the O-benzyl group and glycosylation with the β-chloride 13 under catalysis by silver salts afforded the protected di- to penta-saccharide glycosides 16, 19, 21, and 23, which were conventionally deblocked.Keywords: Pentasaccharide; Polysaccharide II; Mycobacterium tuberculosis