47727-93-5

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4-Tri-O-benzyl-D-glucopyranose is used as an intermediate in the synthesis of 6-Phosphoglucono-δ-lactone (P353740), which serves as a substrate for lactonase enzymes from Mycoplasma synoviae 53 (MS530025) and Mycoplasma agalactiae PG2 (MAG6390). These lactonase enzymes play a crucial role in the metabolism of these bacteria, and the compound is essential for the development of potential therapeutic agents targeting these pathogens.
Additionally, due to its structural similarity to glucose and its modified reactivity, 2,3,4-Tri-O-benzyl-D-glucopyranose may also be utilized in the development of other pharmaceutical compounds, particularly those targeting carbohydrate-binding proteins or enzymes involved in carbohydrate metabolism.

Upstream product

• 65556-30-1 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 35094-58-7 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl bromide 
• 108-24-7 acetic anhydride 
• 89157-97-1 1,6-anhydro-2,3,4-tri-O-benzyl-β-L-idopyranose 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 3150-20-7 4-methoxyphenyl β-D-glucopyranoside 
• 2872-65-3 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 39483-52-8 4-Nitro-benzoic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethyl ester 
• 150584-70-6 Acetic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-(2-benzylsulfanyl-ethoxy)-tetrahydro-pyran-2-ylmethyl ester 
• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 

Downstream Products

• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 73111-53-2 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 68536-37-8 Toluene-4-sulfonic acid (2R,3R,4S,5S)-3,4,5-tris-benzyloxy-6-hydroxy-tetrahydro-pyran-2-ylmethyl ester 
• 187103-77-1 2,3,4-tri-O-benzyl-D-glucitol 
• 641635-63-4 methyl 2,3,4-tri-O-benzyl-α-L-idopyranoside 
• 205192-05-8 methyl 2,3,4-tri-O-benzyl-β-L-idopyranoside 
• 1038507-81-1 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranose 
• 142259-62-9 (Z)-2,4-di-O-benzyl-3-deoxy-D-erythro-hex-2-eno-aldehyde 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 1,6-bis-triazole-2,3,4-tri-O-benzyl-α-D-glucopyranosides as a novel α-glucosidase inhibitor in the treatment of Type 2 diabetes

A novel series of 1,6-bis-triazole-benzyl-α-glucoside derivatives (7a-7ee) were designed, synthesized and evaluated for inhibitory activity against α-glucosidase. Most of the synthesized compounds exhibited good activity with IC50 ranging from

Four Different Regioisomeric Polycarbonates Derived from One Natural Product, d -Glucose

Strategies for the preparation of polycarbonates, derived from the natural product d-glucose, which have the potential to degrade back into their bioresorbable starting material and CO2, were developed. By employing established carbohydrate pro

SGLT-2 INHIBITORS

Provided are compounds of SGLT-2 inhibitors, pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof with

Impact of sugar stereochemistry on natural killer T cell stimulation by bacterial glycolipids

Natural killer T (NKT) cells recognize glycolipids produced by Sphingomonas bacteria, and these glycolipids contain C6-oxidized sugars, either glucuronic acid or galacturonic acid, linked to ceramides. Glycolipids with gluco stereochemistry are the most p

Divergent synthesis of L-sugars and L-iminosugars from D-sugars

An efficient divergent synthesis of L-sugars and L-iminosugars from D-sugars is described. The important intermediate. δ-hydroxyalkoxamate. prepared from D-glucono-/galactono-1,5-lactone, was cyclized under Mitsunobu conditions to give the O-cyclized oxim

Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely α-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by 3JC,H coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective.

Synthesis of the dimethyl ester of 1-deoxy-L-idonojirimycin-1- methylenphosphonate: A new approach to iminosugar phosphonates

1-Methylenphosphonate-1-deoxy-L-idonojirimycin (1) has been synthesized starting from commercially available tetrabenzyl glucose, the key steps being substitution of the hydroxyl group at C-5 of compound 7 with an azido group, stereoselective reaction of

An approach to the highly stereocontrolled synthesis of α-glycosides. Compatible use of the very acid labile dimethoxytrityl protecting group with Yb(OTf)3-promoted glycosidation

The very acid labile dimethoxytrityl group is demonstrated to survive Yb(OTf)3-promoted glycosidations with N-phenyl trifluoroacetimidates as the donors. In addition, the installation of this sterically demanding protecting group at the primary

Azidohalogenobenzyl derivatives, sugar compounds and protection of hydroxy groups

Azidohalogenobenzyl derivatives of the formula (I) STR1 wherein A is a halogen atom, B is a halogen atom or a hydrogen atom, and X is a group reactive with a hydroxy group, methods of protecting hydroxy group(s) using said derivatives, and sugar compounds wherein a hydrogen atom of at least one hydroxy group is substituted by an azidohalogenobenzyl group. According to the present invention, there are provided novel derivatives capable of introducing a group into a compound having hydroxy group(s), which group is useful as a stable hydroxy-protecting group even in solid phase synthesis for the purpose of the extension of sugar chain under continuous acidic conditions and of being removed under mild conditions; sugar compounds protected by using said derivatives; and methods of protecting hydroxy group(s) using said derivatives.

Benzylthioethyl Group as a Base Stable/Base Removable Glycosidic Protecting Group in Oligosaccharide Synthesis

Benzylthioethyl can be used as a glycosidic protecting group and removed by oxidation with dimethyldioxirane followed by base treatment.