1 iodooctane

Potassium hydroxide (>85.5%), zinc acetate dihydrate (>99.0%), ethanol (>99.5%), hydrochloric acid (35%), hexane (>95.0%), ethyl acetate (>99.3%), tetrahydrofuran (>99.5%), dichloromethane (>99.5%) and chloroform-d₁ (99.8% D) were purchased from Kanto Chemical Co., Inc. L1S (>98.0%), L1L (>98.0%), 1-bromodecane (>98.0%), triethyl phosphite (>97.0%), diisopropylamine (>99.0%), n-buthyllitium (1.59 mol L⁻¹ in hexane), 1-iodooctane (>97.0%), bromotrimethylsilane (>95.0%) were purchased from Tokyo Chemical Industry Co., Ltd. All reagents were used without further treatment. The syntheses of L2 and L3 are shown in the ESI.†

1-Iodobutane, 1-iodooctane, 1-iodododecane, 1-iodohexadecane, and 1-iodooctadecane were purchased from Tokyo Chemical Industry Corporation (Tokyo, Japan). L-Ascorbic acid (AA), L-Ascorbic acid sodium salt (AANa), acetyl chloride, chloromethyl methyl ether, potassium carbonate, hydrochloric acid (HCl), oxatomide, and p-nitrophenyl-2-acetamido-2-deoxy-β-D-glucopyranoside (PNAG) were purchased from FUJIFILM Wako Pure Chemical Corporation (Osaka, Japan). Diaion HP20 (Mitsubishi Chemical Corporation, Tokyo, Japan), Wakogel C-200 (FUJIFILM Wako Pure Chemical Corporation), Silica Gel 60 (Merck KGaA, Darmstadt, Germany), and TOYOPEARL HW-40C (Tosoh Corporation, Tokyo, Japan) were utilized for column chromatography. Monoclonal anti-dinitrophenyl antibody (DNP-IgE) and dinitrophenyl-labeled human serum albumin (DNP-HSA) were obtained from Sigma-Aldrich Co., St. Louis, MO, USA. All of the chemicals used were of the highest grade commercially available.