P toluenesulfonyl chloride

All animal experiments were conducted in accordance with humane practices as directed by the Federal Animal Welfare Act, National Institutes of Health (NIH) guidelines, standards of the Association for Assessment and Accreditation of Laboratory Animal Care (AAALAC International), and at the university level under the regulation of the University Committee on the Use and Care of Animals. The protocols were approved by the University of Minnesota Institutional Animal Care and Use Committee.
Poloxamer 188 (Pluronic F68) was generously provided by BASF (Wyandotte, MI). p-Toluenesulfonyl chloride (>99%) was purchased from Acros Organics (Fair Lawn, NJ). Triethylamine (99%), tetrahydrofuran (HPLC grade), N,N-dimethylformamide (DMF) (certified ACS), and dichloromethane (certified ACS) were purchased from Fisher Scientific (Hampton, NH). Sodium azide (>99.5%), triphenylphosphine (99%), α-cyano-4-hydroxycinnamic acid (>98%), sodium trifluoroacetate (98%), and anhydrous N,N-dimethylformamide (99.8%) were purchased from Sigma-Aldrich (St. Louis, MO). Alx647 NHS Ester (N-hydroxysuccinimide ester) was purchased from Thermo Fisher Scientific (Waltham, MA). Molecular sieves (4 Å) were purchased from Mallinckrodt (Staines-upon-Thames, UK). PD-10 desalting columns were purchased from GE Healthcare (Chicago, IL).

Potassium hydroxide (≥85%), sodium
sulfate (anhydrous), sodium hydride (60%, in mineral oil), 2,2,3,3,3-pentafluoro-1-propanol
(97%), 2,2,2-trifluoroethanol (99%), 1 M LiPF₆ in EC/DMC
(50:50 v/v, battery grade), diethylene glycol (99%), triethylene glycol
(99%), tetraethylene glycol (99%), diglyme (anhydrous), α,α,α-trifluorotoluene
(99%), tetraglyme (anhydrous), and 4 Å molecular sieves were
purchased from Sigma-Aldrich. Acetone (99.5%), tetrahydrofuran (certified
grade, with 0.025% butylated hydroxytoluene as a preservative), dichloromethane
(99.5%), hexanes (98.5%), ethyl acetate (99.5%), and methanol (99.8%)
were purchased from Fisher. Lithium foil (750 μm thick), p-toluenesulfonyl chloride (98%), and triglyme (99%) were
purchased from Alfa Aesar. Lithium perchlorate (99%), lithum bis(fluorosulfonyl)
amide (99%), and pentaethylene glycol (95%) were purchased from Oakwood
Chemical. Deuterated acetonitrile (≥99.8 atom % D) and deuterated
chloroform (≥99.8 atom % D) were purchased from Cambridge Isotope
Laboratories. All solvents used for preparing electrolytes were dried
by 4 Å molecular sieves overnight inside an argon-filled glovebox
(VigorTech, O₂ and H₂O < 1 ppm). LiFSA salt
was vacuum-dried at 120 °C overnight in a heated glovebox antechamber
before use and was not exposed to air at any time. Other chemicals
were used as received.