190367-07-8

Usage

Uses

Used in Pharmaceutical Industry:
Phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside is used as a building block for the synthesis of complex carbohydrates, which are essential components in various biological processes and have potential applications in drug development. The compound's unique structure allows for the creation of novel carbohydrate-based drugs with specific targeting and therapeutic properties.
Used in Chemical Synthesis:
In the field of chemical synthesis, phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside serves as an intermediate or starting material for the preparation of various complex carbohydrate structures. Its protecting groups facilitate selective reactions and help in controlling the stereochemistry of the final products, making it a valuable asset in the synthesis of bioactive molecules and natural products.
Used in Research and Development:
Phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-glucopyranoside is also utilized in research and development for studying the structure, function, and interactions of carbohydrates with other biomolecules. Its unique structural features make it an ideal candidate for investigating carbohydrate recognition, binding, and signaling processes, which are crucial for understanding various biological phenomena and developing new therapeutic strategies.

Upstream product

• 71676-30-7 (2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 98-88-4 benzoyl chloride 

Downstream Products

• 1287768-25-5 methyl phenyl 2,3-di-O-benzoyl-4-O-benzyl-1-thio-β-D-glucuronate 
• 1287768-26-6 methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-benzyl-β-D-glucuronate 
• 1287768-28-8 phenyl 2,3-di-O-benzoyl-4,6-O-p-methoxy-benzylidene-1-thio-β-D-glucopyranoside 
• 1287768-29-9 phenyl 2,3-di-O-benzoyl-4-O-p-methoxybenzyl-1-thio-β-D-glucopyranoside 
• 1287768-50-6 C₃₄H₃₀O₉S 
• 1287768-30-2 methyl phenyl 2,3-di-O-benzoyl-4-O-p-methoxybenzyl-1-thio-β-D-glucuronate 
• 1287768-31-3 methyl 1-O-acetyl-2,3-di-O-benzoyl-4-O-p-methoxybenzyl-β-D-glucuronate 
• 1287768-22-2 methyl 2,3-di-O-benzoyl-1-azido-β-D-glucuronate 
• 1287768-18-6 C₅₃H₅₄N₄O₁₄ 
• 1287768-19-7 C₄₃H₄₆N₄O₁₆ 
• 1287768-41-5 C₅₆H₅₆N₄O₁₄ 
• 1287768-43-7 C₅₅H₅₈N₄O₁₅ 
• 1287768-44-8 C₃₆H₃₉N₇O₁₅ 
• 1287768-27-7 phenyl 2,3,-di-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranosyduronic acid 

Relevant academic research and scientific papers

Design and synthesis of unnatural heparosan and chondroitin building blocks

Triazole linked heparosan and chondroitin disaccharide and tetrasaccharide building blocks were synthesized in a stereoselective manner by applying a very efficient copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction of appropriately substituted

Acylation of carbohydrates over Al2O3: Preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides

Selective and per-O-acylation of carbohydrate derivatives using acyl chlorides and Al2O3, a solid support reagent, is reported. This protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

Prearranged glycosides, 9. - Chemical synthesis of a tetrasaccharide fragment related to the exopolysaccharide of Arthrobacter sp. CE-17

The tetrasaccharide 5-aminopentyl glycoside β-D-Manp-(1→4)-β-D-Glcp- (1→4)-α-L-Rhap-(1→3)-β-D-Glcp-1-O-(CH2)5NH2(22) related to the exopolysaccharide of Arthrobacter sp. CE-17 was synthesized by coupling of the properly protected disaccharide blocks β-D-Manp-(1→4)-β-D-Glcp-1-S-Ph (11) and α-L-Rhap-(1→3)-β-D-Glcp-1-O-(CH2)5NHZ (20). Building block 11 was obtained by intramolecular β-mannosylation of a malonyl-tethered disaccharide glycoside which was prepared from phenyl 4,6-O-benzylidene-1- thio-β-D-glucopyranoside (1) and ethyl 2,3,4-tri-O-benzyl-1-thio-α-D- mannopyranoside (5) in 5 steps. Building block 20 was obtained by coupling N- Z-protected 5-aminopentyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (14) obtained from the non-benzylated counterpart 12 with ethyl 2,3-di-O- benzoyl-4-O-chloroacetyl-1-thio-α-L-rhamnopyrano- side (18) obtained in 3 steps from ethyl 2,3-O-isopropylidene- 1-thio-α-L-rhamnopyranoside (15).

Silylmethylene radical cyclization. A stereoselective approach to branched sugars

Ethyl 6-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (2) was converted, in three steps and in 73percent overall yield, into ethyl 6-O-benzyl-2,3-dideoxy-3-C-(hydroxymethyl)-α-D-ribo-hex-2-enopyranoside.This transformation involved silylation of 2