785806-29-3

Upstream product

• 10257-28-0 D-Galactose 
• 108-98-5 thiophenol 
• 100-39-0 benzyl bromide 
• 3866-62-4 1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside 
• 14365-16-3 bis-(phenylthio)-dibutylstannane 
• 13992-16-0 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-galactopyranoside 
• 25878-60-8 D-galactose pentaacetate 

Downstream Products

• 1379442-52-0 methyl 3-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 1379442-54-2 methyl 3-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 4291-68-3 (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 82598-84-3 2,3,4,6-tetra-O-benzyl-D-galactonolactone 
• 1595290-43-9 C₃₈H₄₀O₅ 
• 1595290-24-6 C₄₀H₄₄O₅ 
• 132014-06-3 1-(phenylsulfonyl)-3,4,6-tri-O-benzyl-D-galactal 

Relevant academic research and scientific papers

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Synthesis of Galactosylated Glycosylphosphatidylinositol Derivatives from Trypanosoma brucei

Trypanosoma brucei uses variant surface glycoproteins (VSGs) to evade the host immune system and ensure parasitic longevity in animals and humans. VSGs are attached to the cell membrane by complex glycosylphosphatidylinositol anchors (GPI). Distinguishing structural feature of VSG GPIs are multiple α- and β-galactosides attached to the conserved GPI core structure. T. brucei GPIs have been associated with macrophage activation and alleviation of parasitemia during infection, acting as disease onset delaying antigens. Literature reports that link structural modifications in the GPIs to changes in biological activity are contradictory. We have established a synthetic route to prepare structurally overlapping GPI derivatives bearing different T. brucei characteristic structural modifications. The GPI collection will be used to assess the effect of galactosylation and phosphorylation on T. brucei GPI immunomodulatory activity, and to perform an epitope mapping of this complex glycolipid as potential diagnostic marker for Trypanosomiasis. A strategy for the synthesis of a complete α-tetragalactoside using the 2-naphthylmethyl protecting group and for subsequent attachment of GPI fragments to peptides is presented.

Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction

Anomeric gem-diallylation, mono-β-crotylation and mono-β- propargylation of sugar 1,5 and 1,4 lactones have been achieved under Barbier reaction conditions using Zn powder and a catalytic amount of TMSCl as an activator. Ring closing olefin metathesis of the synthesized gem-diallyl derivatives furnished C-spiro cyclopentene glycosides. Finally, the cyclopentene rings were converted into carbohydrate based tricyclic morpholine fused triazole glycoconjugates as potential SGLT2 inhibitors.

Acceptor-influenced and donor-tuned base-promoted glycosylation

Base-promoted glycosylation is a recently established stereoselective and regioselective approach for the assembly of di- and oligosaccharides by using partially protected acceptors and glycosyl halide donors. Initial studies were performed on partially methylated acceptor and donor moieties as a model system in order to analyze the key principles of oxyanion reactivities. In this work, extended studies on base-promoted glycosylation are presented by using benzyl protective groups in view of preparative applications. Emphases are placed on the influence of the acceptor anomeric configuration and donor reactivities.

Activation and synthetic applications of thiostannanes. A new method for synthesis of thio- and selenoglycosides

Exposure of thiostannane to acetyl or methyl glycosides in the presence of a catalytic amount of Bu2Sn(OTf)2 provides thioglycosides in good yields. Selenoglycosidation is achieved in a like manner by use of selenostannane.