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15 protocols using p 2200

1

Purification and Characterization of Organic Compounds

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All commercial reagents were used as received. Column chromatography was carried out on 60 N silica gel (Kanto Chemicals). Optical rotations were recorded on JASCO P-2200 digital polarimeter. 1H- and 13C-NMR spectra were recorded on Bruker DRX-500 or Bruker AMX-500 spectrometer (500 MHz for 1H-NMR and 125 MHz for 13C-NMR). NMR spectra were recorded in C6D6 (99.5 atom% enriched, Kanto). 1H chemical shifts were reported in δ value based on residual benzene (7.15 ppm) as a reference. 13C chemical shifts were reported in δ value based on benzene (128.0 ppm) as a reference. Data are reported as follows: chemical shift, multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, m = multiplet, br = broad), coupling constant (Hz), and integration. GC-MS analyses were conducted with MS-2010 (Shimadzu). Mass spectra were obtained with a JEOL JMS-T100GCV (EI mode).
Oligonucleotides for polymerase chain reactions (PCRs) were purchased from Hokkaido System Science Co., Ltd. PCRs were performed with a BioRad S1000 thermal cycler.
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2

Spectroscopic Characterization of Compounds

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Optical rotations were measured on a JASCO P-2200 digital polarimeter. CD spectra were recorded on JASCO J-820 spectrometer. Infrared spectra (IR) were obtained with a Thermo Fisher Scientific NICOLET iS5 FT-TR spectrometer from samples in CH2Cl2. NMR spectra were measured on JEOL JMN-ECA600 and JMN-ECS400 spectrometers with tetramethylsilane as an internal standard, and chemical shifts are stated as δ values. HRMS data were recorded on a JMS-700 MStation quadrupole (FAB) or JMS-T100TD TOF (DART) mass spectrometer. A crystal of the compound was measured on a R-AXIS RAPID II (Rigaku). Analytical and preparative TLC were carried out on precoated silica gel 60F254 and RP-18F254 plates (0.25 or 0.50 mm thickness; Merck). MPLC was performed on Combiflash Rf (Teledyne Isco) with silica gel and C18 cartridges (Biotage, Uppsala Sweden). Preparative HPLC was operated on a GL Science recycling system using an InertSustain C18 column (5 μm, 20 × 250 mm).
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3

Characterization of Organic Compounds

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Optical rotations were measured on a JASCO P-2200 digital polarimeter. ECD spectra were recorded on a JASCO J-820 spectrometer. Infrared spectra (IR) were recorded on a Thermo Fisher Scientific NICOLET iS5 FT-TR spectrometer with samples in CH2Cl2. NMR spectra were obtained on JEOL JMN-ECA600 and JMN-ECS400 NMR spectrometers with tetramethylsilane as an internal standard, and chemical shifts are indicated as δ values. HRMS data were recorded on a JEOL JMS-700 (FAB) mass spectrometer. MPLC was performed with C18 cartridges (ODS-25, YMC-DispoPack). Preparative HPLC was conducted on a GL Science recycling system using an InertSustain C18 column (5 μm, 20 × 250 mm) and a CHIRAL ART Cellulose-SC column (5 μm, 10 × 250 mm, YMC).
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4

Analytical Methods for Compound Characterization

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Optical rotations were determined on a JASCO P-2200 digital polarimeter. ECD spectra were measured on a JASCO J-820 spectrometer. Infrared spectra (IR) were recorded with a Thermo Fisher Scientific NICOLET iS5 FT-TR spectrometer with samples in CH2Cl2. NMR spectra were obtained on JEOL JMN-ECA600 and JMN-ECS400 NMR spectrometers with tetramethylsilane as an internal standard, and chemical shifts are stated as δ values. HRMS data were recorded on a JMS-SX102A (FAB) or JMS-T100TD (DART) mass spectrometer. Analytical and preparative TLC were performed on precoated silica gel 60F254 and RP-18F254 plates (0.25 or 0.50 mm thickness; Merck). MPLC was performed on a Combiflash Rf (Teledyne Isco) instrument with silica gel and C18 cartridges (ODS-25, YMC-DispoPack). Preparative HPLC was conducted on a GL Science recycling system using an InertSustain C18 column (5 µM, 20 × 250 mm).
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5

Spectroscopic Characterization of Organic Compounds

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Optical rotations were measured on a JASCO P-2200 digital polarimeter. NMR spectra were recorded on JEOL JMN-ECS400 and JMN-ECA600 spectrometers with tetramethylsilane as an internal standard. Chemical shifts are expressed as δ values. HRMS data were obtained on a JMS-SX102A (FAB) or JMS-T100TD (DART) mass spectrometer. Analytical and preparative TLC were carried out on precoated silica gel 60F254 and RP-18F254 plates (0.25 or 1.0 mm thickness; Merck).
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6

Spectroscopic Characterization of Organic Compounds

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Optical rotations were recorded on a JASCO P-2200 digital polarimeter. Infrared spectra (IR) were measured with a Shimadzu FTIR-8700 instrument for samples in CHCl3. NMR spectra were taken on a JEOL JMN-ECA600 spectrometer and JMN-ECS400 spectrometer with tetramethylsilane as an internal standard, and chemical shifts are expressed as δ values. High-resolution mass spectrometric data were obtained on a JEOL JMS-700 (FAB) or a JMS-T100TD (DART) mass spectrometer. Analytical and preparative TLC was carried out on precoated silica gel 60F254 and RP-18F254 plates (0.25 or 0.50 mm thickness; Merck). MPLC was performed with silica gel and C18 cartridges (Biotage, Uppsala, Sweden).
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7

Characterization of Synthetic Compounds

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Optical rotations were recorded on a JASCO P-2200 digital polarimeter. Infrared spectra (IR) were measured with a Shimadzu FTIR-8700 instrument for samples in CHCl3. NMR spectra were acquired on JEOL JMN-ECA600 and JMN-ECS400 spectrometers with tetramethylsilane as internal standard, and chemical shifts are expressed as δ values. HRMS data were obtained on a JMS-SX102A (FAB) or JMS-T100TD (DART) mass spectrometer. Microwave irradiation experiments were carried out in a dedicated Biotage Initiator 2.5 microwave apparatus. Analytical and preparative TLC was carried out on precoated silica gel 60F254 and RP-18F254 plates (0.25 or 0.50 mm thickness; Merck). MPLC was performed with silica gel and C18 cartridges (Biotage, Uppsala Sweden). Compounds 91316 ,17 (link),20 and 1921 (link) were obtained previously.
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8

Characterization of Organic Compounds

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Optical rotations were recorded on a JASCO P-2200 digital polarimeter. Infrared spectra (IR) were measured with a Shimadzu FTIR-8700 instrument for samples in CHCl3. NMR spectra were recorded on JEOL JMN-ECA600 and JMN-ECS400 spectrometers with tetramethylsilane as an internal standard, and chemical shifts are expressed as δ values. HRMS data were obtained on a JMS-SX102A (FAB) or JMS-T100TD (DART) mass spectrometer. Analytical and preparative TLC were carried out on precoated silica gel 60F254 and RP-18F254 plates (0.25 or 0.50 mm thickness; Merck). MPLC was performed with silica gel and C18 cartridges (Biotage, Uppsala Sweden).
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9

Spectroscopic Analysis of Chemical Compounds

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Optical rotations were measured on a JASCO P-2200 digital polarimeter in CHCl3. NMR spectra were recorded on JEOL JNM-ECS400 and JNM-ECA600 NMR spectrometers with tetramethylsilane as an internal standard, and chemical shifts are stated as δ values. HRMS data were measured on a JMS-700 (FAB) or JMS-T100TD (DART) mass spectrometer. UV spectra were recorded on a Tecan SPARK 10M in CH3CN–H2O (1:1) except for compound 2 in CH3CN. IR spectra were measured neat on a Shimadzu IRSprit. Preparative HPLC was performed on a GL Science recycling system using InertSustain C18 (5 μm, 20 × 250 mm) and chiral ART Cellulose-SC (5 μm, 250 × 10.0 mm) columns. Analytical and preparative TLC were carried out on precoated silica gel 60 F254 plates (0.25 or 1 mm thickness; Merck) and an NH2 silica gel 60 F254 plate (0.5 mm; Wako). Column chromatography was conducted with silica gel 60 N (Spherical, 63–210 μm, neutral, Kanto Chemical). Analytical and reversed-phase preparative TLC were performed on silica gel 60 RP-18 F254S (0.25 mm, Merck).
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10

Optical Rotation of CMA Isomers

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R- and S-CMA were dissolved in 1 M HCl to prepare 0.46 and 0.48 w/v% solutions, respectively. The optical rotation of each solution was measured with a P-2200 digital polarimeter (Jasco Corporation, Tokyo, Japan) using a 100-mm quartz cell.
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