78880-58-7

Upstream product

• 576-26-1 2.6-dimethylphenol 
• 96863-21-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate 
• 59980-96-0 Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 931-59-9 benzenesulfenyl chloride 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Relevant academic research and scientific papers

Reengineering Chemical Glycosylation: Direct, Metal-Free Anomeric O-Arylation of Unactivated Carbohydrates

To sustain innovation in glycobiology, effective routes to well-defined carbohydrate probes must be developed. For over a century, glycosylation has been dominated by the formation of the anomeric Csp3?O acetal junction in glycostructures. A dissociative mechanistic spectrum spanning SN1 and SN2 is frequently operational thereby reducing the efficiency. By reengineering this fundamental process, an orthogonal disconnection allows the acetal to be formed directly from the reducing sugar without the need for substrate pre-functionalisation. The use of stable aryliodonium salts facilitates a formal O?H functionalisation reaction. This allows lactols to undergo mild, metal-free O-arylation at ambient temperature. The efficiency of the transformation has been validated using a variety of pyranoside and furanoside monosaccharides in addition to biologically relevant di- and trisaccharides (up to 85 %). Fluorinated mechanistic probes that augment the anomeric effect were employed. It is envisaged that this strategy will prove expansive for the construction of complex acetals under substrate-based stereocontrol.

Selective formation of β-O-aryl glycosides in the absence of the C(2)-ester neighboring group

(Chemical Equation Presented) The development of a general and practical method for the stereoselective synthesis of β-O-aryl glycosides that exploits the nature of a cationic palladium(II) catalyst, instead of a C(2)-ester directing group, to control the

A stable, commercially available sulfenyl chloride for the activation of thioglycosides in conjunction with silver trifluoromethanesulfonate

p-Nitrobenzenesulfenyl chloride is a stable commercially available sulfenyl chloride that, in conjunction with silver triflate, cleanly activates a wide range of thioglycosides for glycosylation at -78 °C in CH2Cl2.

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.

New Synthetic Methods and Reagents for Complex Carbohydrates. IX. Aryl D-Glucopyranosides and 1-Aryl-1-deoxy-D-glucopyranoses from 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl Dimethylphosphinothioate

The reactions of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate and phenolic compounds gave the corresponding aryl α-D-glucopyranosides predominantly in good yields, even when the trimethylsiloxy derivatives of benzene, which are known