84224-65-7

Basic information

• Product Name: Benzenesulfenyl Triflate
• Synonyms: Benzenesulfenyl Triflate
• CAS NO: 84224-65-7
• Molecular Formula: C₇H₅F₃O₃S₂
• Molecular Weight: 258.2380096
• Mol File: 84224-65-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzenesulfenyl Triflate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfenyl Triflate(84224-65-7)
• EPA Substance Registry System: Benzenesulfenyl Triflate(84224-65-7)

Safety Data

• Hazardous Substances Data: 84224-65-7(Hazardous Substances Data)

Upstream product

• 2923-28-6 silver trifluoromethanesulfonate 
• 931-59-9 benzenesulfenyl chloride 

Downstream Products

• 59980-96-0 Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 314740-77-7 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl triflate 

Relevant articles and documents

Highly diastereoselective α-mannopyranosylation in the absence of participating protecting groups

S-Phenyl 2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)- 1- thia-α-D-mannopyranoside and its sulfoxide, following activation at -78 °C with benzenesulfenyl triflate or trifiic anhydride, respectively, provide the corresponding α-mannosyl triflate as demonstrated by NMR spectroscopy. On addition of an acceptor alcohol α-mannosides are then formed. Similarly, S- phenyl 2,3-O-carbonyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside and ethyl 3-O-benzoyl-4,6-O-benzylidene-2-O-(tert-butyldimethylsilyl)-1-thia-α-D- mannopyranoside both provide α-mannosides on activation with benzenesulfenyl triflate followed by addition of an alcohol. These results stand in direct contrast to the highly β-selective couplings of comparable glycosylations with 2,3-di-O-benzyl-4,6-O-benzylidene protected mannosyl donors and draw attention to the subtle interplay of reactivity and structure in carbohydrate chemistry.

Are glycosyl triflates intermediates in the sulfoxide glycosylation method? A chemical and 1H, 13C, and 19F NMR spectroscopic investigation

The title question is addressed by low-temperature 1H, 13C, and 19F NMR spectroscopies in CD2CL2 as well as by the preparation of authentic samples from glycopyranosyl bromides and AgOTf. At -78°C glycosyl triflates are cleanly generated with either nonparticipating or particpating protecting groups at O-2. The glycosyl triflates identified in this manner were allowed to react with methanol, resulting in the formation of methyl glycosides. Glycosyl triflates were generated at -78°C in CD2Cl2 and allowed to warm gradually until decomposition was detected by 1H and 19F NMR spectroscopy. The decomposition temperature and products are functions of the protecting groups employed.

Synthesis and Reactions of Sulfenic Trifluoromethanesulfonic Anhydrides

Sulfenyl halogenides 1 and 4 react with silver trifluoromethanesulfonate (2) to give aryl 3 and alkylsulfenic trifluoromethanesulfonic anhydrides 5, resp., in good yields; 3 and 5 could not be isolated because of their instability. 1H NMR spectroscopic data of 5a, b, each in dichloromethane and nitromethane, resp., are indicative of a dissoziation to adducts of alkylsulfenylium ions and the solvent.Whereas 3 do not react with aromatic compounds, addition products with diphenylacetylene, arylsulfenylvinyl trifluoromethanesulfonates 11, are formed smoothly, which under the reaction conditions immediately cyclize to give benzothiophenes 10 in excellent yields.