188357-34-8

Usage

Uses

Used in the Direct Synthesis of β-Mannopyranosides:
Ethyl2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranosideS-oxide is used as a key intermediate in the direct synthesis of β-mannopyranosides by the sulfoxide method. This method is a valuable approach in the field of carbohydrate chemistry, as it allows for the efficient and selective synthesis of β-mannopyranosides, which are important structural components in various biological systems.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ethyl2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranosideS-oxide can be used as a building block for the development of novel drugs targeting various diseases. Its unique chemical structure and reactivity make it a promising candidate for the synthesis of complex carbohydrate-based therapeutics.
Used in Chemical Research:
Ethyl2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranosideS-oxide is also used in chemical research, particularly in the study of carbohydrate chemistry and the development of new synthetic methods. Its unique structure and properties make it an interesting subject for researchers to explore and potentially discover new applications and reactions.
Used in Material Science:
In the field of material science, Ethyl2,3-di-O-benzyl-4,6-O-benzylidene-a-D-thiomannopyranosideS-oxide may find applications in the development of new materials with specific properties, such as improved biocompatibility or enhanced chemical stability. Its unique structure and reactivity could contribute to the creation of novel materials with potential applications in various industries.

InChI:InChI=1/C29H32O6S/c1-2-36(30)29-27(32-19-22-14-8-4-9-15-22)26(31-18-21-12-6-3-7-13-21)25-24(34-29)20-33-28(35-25)23-16-10-5-11-17-23/h3-17,24-29H,2,18-20H2,1H3/t24?,25-,26+,27-,28?,29-,36?/m1/s1

Upstream product

• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 153062-17-0 S-ethyl 4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside 
• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 100-52-7 benzaldehyde 
• 142924-31-0 S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 
• 218937-71-4 ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 

Relevant academic research and scientific papers

Synthesis of 12- O-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle

Fifteen glycosyl-oxystearates were synthesized by Crich's 4,6-benzylidene and K?ening-Knorr strategies. Assessment of structure-activity relationships using macrophage-inducible C-type lectin (Mincle) receptor cells expressing nuclear factor of activated

Stereoselective formation of glycosyl sulfoxides and their subsequent equilibration: Ring inversion of an α-xylopyranosyl sulfoxide dependent on the configuration at sulfur

A series of four S-allyl D-thiopyranosides, α- and β-manno and xylo, were oxidized with MCPBA at low temperature to give seven of the eight possible sulfoxides, whose configuration at sulfur was determined either directly by X-ray crystallography or by co

Direct chemical synthesis of β-mannopyranosides and other glycosides via glycosyl triflates

High yield, highly stereoselective methods for the synthesis of β- mannopyranosides primary, secondary, and tertiary alcohols are presented. Activation of mannosyl sulfoxides or mannosyl thioglycosides with trifluoromethanesulfonic anhydride or benzenesulfenyl triflate, respectively, leads to the efficient formation of α-mannosyl triflates at -78 °C in dichloromethane, in the presence of 2,6-di-tertbutyl-4-methylpyridine. These triflates then react S(N)2-like with alcohols to give the β-mannosides. The use of a 4,6-O-benzylidene protected mannose is required for high selectivity, as is the use of non-participating protecting groups on O-2 and O-3 of the donors. It is further demonstrated that the thioglycoside/benzensulfenyl triflate activation is applicable in the glucoside series, when both armed and disarmed protecting groups are tolerated.

Stereoselective sulfoxidation of α-mannopyranosyl thioglycosides: The exo-anomeric effect in action

As a consequence of the exo-anomeric effect, and in contrast to their β-anomers, α-thioglycosides undergo stereoselective oxidation to give very predominantly the R-sulfoxides, as revealed by X-ray crystallography.