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CAS No. : | 24259-59-4 | MDL No. : | MFCD00167010 |
Formula : | C5H10O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PYMYPHUHKUWMLA-MROZADKFSA-N |
M.W : | 150.13 | Pubchem ID : | 90428 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.8 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 31.0 |
TPSA : | 97.99 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.86 cm/s |
Log Po/w (iLOGP) : | -0.76 |
Log Po/w (XLOGP3) : | -2.32 |
Log Po/w (WLOGP) : | -2.74 |
Log Po/w (MLOGP) : | -2.48 |
Log Po/w (SILICOS-IT) : | -1.29 |
Consensus Log Po/w : | -1.92 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | 0.95 |
Solubility : | 1350.0 mg/ml ; 9.01 mol/l |
Class : | Highly soluble |
Log S (Ali) : | 0.8 |
Solubility : | 944.0 mg/ml ; 6.29 mol/l |
Class : | Highly soluble |
Log S (SILICOS-IT) : | 1.94 |
Solubility : | 13000.0 mg/ml ; 86.9 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.81 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
molybdenum(VI) oxide; In water; at 96℃; for 2h;pH <= 2.9 - 3.4;Conversion of starting material; | EXAMPLE 8; Epimerization of the Arabinose Fraction Obtained from Chromatographic Fractionation of Example 2(B); The arabinose fraction obtained from the chromatographic fractionation as described in Example 2(B) was epimerized in a laboratory scale stirred reaction vessel. The volume of the reaction vessel was 1 l and it was provided with a heating jacket. The concentration of the solution was adjusted to 14 g/l 00 g, and 900 ml of this solution having about 87percent on DS of L-arabinose was transferred to the reaction vessel. 1.36 g of MoO3 was used as the epimerization catalyst and the reaction time at 96° C. was 2 hours. The pH was adjusted to be 2.9 at the end of the reaction. About 29.5percent of the available arabinose was converted in the reaction. 78percent of the reacted arabinose was converted to L-ribose. The resulting epimerized solution had an L-ribose content of about 20percent on DS.; EXAMPLE 9; Epimerization of Crystalline Arabinose; Crystalline L-arabinose obtained from the crystallization of Example 7 was dissolved in water to obtain 900 ml of a solution having an arabinose concentration of 13.2 g/100 g. The solution was transferred to a laboratory scale stirred reaction vessel. The volume of the reaction vessel was 1 l and it was provided with a heating jacket. 1.26 g of MoO3 was weighed as a catalyst for the epimerization reaction. At the beginning of the reaction, the pH was adjusted to 3.4 with NaOH. The epimerization was carried out at a temperature of 96° C. for 2 hours. About 33percent of the arabinose was converted during the reaction. 76percent of the reacted arabinose was converted to L-ribose. The resulting epimerized solution had an L-ribose content of about 25percent on DS. | |
With borax; In water; at 69.84℃; for 1h;Kinetics; | For the factorial design experiments, Sn-Beta (Si/Sn = 96) wasadded at a 100:1 sugar?metal molar ratio to a 5 wtpercent sugar solutionin a 5 ml thick-walled glass reactor containing a small magneticstir bar (typically ?40 mg of catalyst in 2 ml of sugar solution).Reactions were performed with D- and L-arabinose interchangeably with no difference in kinetics. Initial rate experiments weredone with larger volumes and higher sugar?metal ratios in orderto capture the low conversion data points. In order to determinethe initial rates at higher temperature ranges, an arabinose to Snratio of 1000 or 2000 was used. The thick-walled glass vials weresealed using a PTFE/silicone septa and metal crimp top, placed in atemperature-controlled oil bath, and removed periodically to takesamples. The glass reactors were quenched in ice and a small sam-ple volume was removed. Next, 100 l of the filtered sample and25 l of a 10 wtpercent mannitol solution were mixed in a vial. The sam-ples were analyzed by high-performance liquid chromatography(HPLC) on an Agilent 1260 system equipped with photodiode arrayultraviolet and evaporative light-scattering detectors. The reactionproducts were separated using a Bio-Rad Aminex HPX-87C columnheated to 353 K using deionized water (pH = 7) as the mobile phaseat a flow rate of 0.6 ml min?1. Ribulose concentrations were deter-mined using an ultraviolet detector at a wavelength 210 nm. At thiswavelength all other sugars had negligible ultraviolet signals. Forall ultraviolet-inactive carbohydrates, the analysis was performedusing the evaporative light scattering detector. Samples were runin duplicate on the HPLC and the column was regenerated dailywith 0.1 M Ca(NO3)2. Ketoses showed the strongest tendency toshift retention time in the column. Fractionation and NMR wereused to check peak purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Example 9 Synthesis of L-ribose 1-O-benzyl-2,3-O-isopropylidene-L-ribonofuranoate (10 g) prepared in Example 7 was dissolved in 3percent TFA solution (30 ml) and reacted under reflux for 3 hours. After TLC revealed the completion of reaction, the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=4/1, v/v) to give the title compound (4.5 g, Yield 84percent). | |
70% | Example 3 Synthesis of L-ribose 2,3-O-isopropylidene-L-ribofuranose (4.0 g) prepared in Example 2 was dissolved in a solvent mixture of dioxane (8 ml) and water (8 ml), and 1.0N hydrochloric acid solution (200 mul) was added thereto. The reaction proceeded for about 24 hours while maintaining the temperature in the reaction vessel of 40° C. After TLC revealed the completion of reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in water (15 ml) which was then washed with ethyl acetate to remove some impurities. Water was removed by distillation under reduced pressure to give a compound in the form of an oil. The compound thus obtained was purified by silica gel column chromatography (eluent: chloroform/methanol=4/1, v/v) to give the title compound (2.2 g, Yield 70percent). | |
Compounds of formula IV include:possibly substituted aliphatic diols such as...D(+)-arabitol,L(-)-arabitol,5-deoxy-L-arabinose,D(-)-ribose,L(+)-ribose,2-deoxy-ribose,D(+)-xylose,L(-)-xylose,... |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
This compound is prepared from <strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> according to Recondo and Rinderknecht (loc. cit.) who prepared 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (1, R1=Ac, R2=Bz) from <strong>[24259-59-4]D-<strong>[24259-59-4]ribose</strong></strong>. A mixture of <strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (150 g, 1.0 mol) in methanol (2.5 L) containing 1percent hydrogen chloride is stirred for 2 hours, and then neutralized with pyridine (250 mL). The mixture is concentrated in vacuo, and the residue dissolved in pyridine (1 L). To the solution is added benzoyl chloride (385 mL, 3.3 mol) dropwise while chilling to 0° C. After being kept overnight at room temperature, the mixture is concentrated in vacuo at 35-40° C. , and the residue is dissolved in ethyl acetate (1.5 L). The organic solution is washed successively with cold water (2.x.0.5 L), 1N H2SO4 (3.x.0.5 mL), water (0.5 L), saturated sodium bicarbonate (2.x.0.5 mL), dried over magnesium sulfate, concentrated in vacuo to a syrup which is dissolved in a mixture of glacial acetic acid (200 mL) and acetic anhydride (0.5 L). To the solution is added concentrated sulfuric acid dropwise at 0° C. The product solidified is filtered, washed successively with cold water (2.x.0.5 L), saturated sodium bicarbonate (2.x.0.5 L), cold water (2.x.0.5 L), and recrystallized from methanol to give compound 1 (225 g, 45percent), mp 124-125° C. . The 1H-NMR spectrum of this sample is identical to that of the D-isomer. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sulfuric acid; acetic anhydride; sodium hydrogencarbonate; In pyridine; methanol; hexane; chloroform; acetic acid; ethyl acetate; | Example 13 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-L-ribofuranose (5) To a solution of L-ribose (25.0 g, 166.66 mmol) in MeOH (300 mL), was added 25 mL of sat. methanolic hydrogen chloride and stirred at room temperature for 6 h. The reaction was complete after 6 h as indicated by TLC using CH2 Cl2/ MeOH 9:1. After completion of the reaction, dry pyridine (30 mL) was added and the solvents were evaporated. To the residue another 30 mL of pyridine was added and evaporated to dryness. The residue was dissolved in dry pyridine (200 mL) and CH2 Cl2 (150 mL) then cooled to 0 ° C. Benzoyl chloride (96.26 mL, 830.12 mmol) was added drop-wise and stirred at room temperature overnight. TLC using hexane/ethyl acetate (7:3), indicated completion of the reaction. The solvents were evaporated and the residue dissolved in CHCl3 (300 mL), and washed with H2 O (200 mL) and sat. NaHCO3 (200 mL), and dried over anhydrous Na2 SO4. After evaporating the CHCl3, the residue was co-evaporated with toluene to give an oily residue. The residue was dissolved in AcOH (200 mL), acetic anhydride (85.0 mL; 770.9 mmol) and sulfuric acid (4.46 mL; 83.29 mmol). The reaction mixture was stirred at room temperature overnight, after which time TLC (hexane/ethyl acetate 7:3) indicated completion of the reaction. The solvents were evaporated in vacuo and the residue that obtained was co-evaporated with toluene. The brown residue was triturated with EtOH to give light brown crystals. Filtration of the solid and recrystallization from EtOH gave 1-O -acetyl-2,3,5-tri-O-benzoyl-L(+)-glucofuranose 40.5 g (48.0percent) as white crystals: mp 125-125° C.; 1 H NMR (CDCl3) delta 4.49 (m, 1H, C5' H), 4.77 (m, 2H, C4' H and C5' H), 5.80 (d, 1H), 5.93 (m, 1H, C2' H), 6.43 (d, 1H, C1' H, J1,2 =1.5 Hz) and 7.30-8.09 (m, 15H, PhH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34.5 g (90%) | With iodine; In dichloromethane; chloroform; ethyl acetate; acetone; | Example 4 2,3-O-Isopropylidene-<strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (22) To a stirred suspension of <strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (30.0 g, 260 mmol) in dry acetone (200 mL) was added iodine (1.27 g, 10 mmol) at room temperature under argon atmosphere. The reaction mixture was stirred for 1 h (the solution becomes homogeneous during this period) and quenched with sodium thiosulfate solution (1 M). The solution was evaporated to dryness. The residue was dissolved in CH2 Cl2 (250 mL), dried over anhydrous MgSO4, filtered and the solid was washed with CH2 Cl2 (150 mL). The combined filtrate was evaporated to dryness. The residue was placed on top of silica column (8*116 cm) packed in CHCl3. The column was eluted with CHCl3 (500 mL), CHCl3:EtOAc (9:1, 1000 mL) and CHCl3: EtOAc (7.3. 1500 mL). The pure product eluted in CHCl3: EtOAc (7:3) was collected and evaporated to give an oily residue 34.5 g (90percent). The oily product used as such for the next reaction. 1 H NMR (CDCl3) delta 1.30 and 1.38 (2s, 6H, isopropylidene CH3), 3.70 (m, 3H), 4.08 (m, 1H), 4.38 (m, 1H), 4.55 (d, 1H), 4.81 (d, 1H) and 5.38 (m, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; sulfuric acid; In methanol; | Example 11 Methyl 2,3-isopropylidene-beta-L-ribofuranoside <strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (15.5 g, 98 mmol) was combined with methanol (150 mL) and concentrated sulfuric acid (0.5 mL). This solution was stirred at ice bath temperature for 18 h. 2,2-Dimethoxypropane (300 mL) was added to the solution and stirring was continued at ambient temperature for 18 h more. Pyridine (40 mL) was added and the solution was concentrated. The residue was partitioned between ethyl acetate (300 mL) and 1N HCl (4*100 mL), and then the organics were washed with 10percent NaHCO3, dried with Na2SO4, decanted and concentrated. The residue was a gold oil 20.0 g, 98 mmol, 95percent); [alpha]20D=(+) 92.0 (c=0.5 DMP); MS (CI): m/z (rel. intensity) 2.05 (58.28, M+); 1H NMR (DMSO d6) delta4.85 (s, 1H, H-1), 4.80 (d, 1H, H-2, J=6.0 Hz), 4.51 (d, 1H, H-3, J=6.0 Hz), 3.98 (t, 1H, H-4, J=5.8 Hz, J=8.9 Hz), 3.37-3.26 (m, 2H, H-5), 3.19 (s, 3H, OMe), 1.36 (s, 3H, CH3), 1.23 (s, 3H, CH3). Anal. Calcd. for C9H16O5: C, 52.93; H, 7.90. Found: C, 52.90; H, 7.88. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; dichloromethane; at 40℃; for 48h; | Aglycon 7 (30 mg, 0.055 mmol) was placed into a 1 dram vial, dissolved in CH2Cl2 (100 muL), and the volume adjusted with methanol (600 muL). After adding <strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (41 mg, 0.27 mmol), the reaction was capped, warmed to 4OC and allowed to stir for 2 d. Solvent was subsequently removed in vacuo and the resulting crude solid suspended in 5:95 methanol: CH2Cl2 (250 muL) by sonication. The mixture was purified by column chromatography (SiO2, MeOH:CH2Cl2 5:95), providing the white solid neoglycoside as a mixture of anomers (18 mg, 49percent, Rf = 0.23 MeOH:CH2C12 5:95). IH NMR (CD3OD, 400 MHz) delta 4.71 (d, J= 1.9 Hz, 1 H), 4.61 (d, J= 3.8 Hz, 0.33 H, alpha-Hl), 4.59 (s, 1 H), 4.55 (m, 1 H), 4.39 (d, J = 8.8 Hz, 0.67 H, beta-Hl), 4.12-4.09 (m, 1.34 H, 2beta), 3.98 (t, J= 5.6 Hz, 0.33 H, alpha), 3.87 (td, J= 5.6, 3.7 Hz, 0.33 H, alpha), 3.78-3.75 (m, 0.33 H, alpha), 3.74-3.70 (m, 0.66 H, 2 alpha), 3.69-3.65 (m, 0.67 H, beta), 3.65 (s, 2 H), 3.61 (s, 3 H), 3.60-3.57 (m, 0.67 H, beta), 3.52 (dd, J = 8.8, 2.9 Hz, 0.67 H, beta), 3.03 (td, J = 10.7, 4.7 Hz, 1 H), 2.31 (td, J = 12.6, 3.4 Hz, 1 H), 2.23 (dt, J = 12.6, 3.2 Hz, 1 H), 1.99-1.87 (m, 2 H), 1.77-1.59 (m, 10 H), 1.57-1.50 (m, 2 H), 1.49-1.36 (m, 7 H), 1.32-1.27 (m, 1 H), 1.21-1.14 (m, 1 H), 1.08 (dd, J= 12.9, 4.4 Hz, 1 H), 1.02 (s, 3 H), 0.98 (s, 3 H), 0.90 (s, 3 H), 0.88 (s, 6 H), 0.84 (m, 1 H); 13C NMR (CD3OD, 100 MHz) delta 180.18, 172.61, 152.12, 110.35, 100.88 (alpha-Cl), 91.67 (beta-Cl), 85.13 (alpha), 83.35, 73.36 (alpha), 72.54 (beta), 72.30 (beta), 69.01 (beta), 68.64 (beta), 66.00, 64.16 (alpha), 62.96 (alpha), 62.40, 57.63, 56.99, 55.31, 52.03, 50.58, 48.64, 43.77, 42.10, 39.77, 39.14, 38.45, 38.29, 35.63, 33.50, 31.86, 31.00, 28.61, 26.99, 24.86, 22.28, 19.72, 19.44, 17.16, 16.91, 16.79, 15.32; HRMS (ESI) m/z for C38H61NNaO9 ([M+Na]+) 698.4232, calc. 698.4239 (Fig. 8A-D). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With borax; In water; at 69.84℃; for 0.75h;Kinetics; | For the factorial design experiments, Sn-Beta (Si/Sn = 96) wasadded at a 100:1 sugar?metal molar ratio to a 5 wtpercent sugar solutionin a 5 ml thick-walled glass reactor containing a small magneticstir bar (typically ?40 mg of catalyst in 2 ml of sugar solution).Reactions were performed with D- and L-arabinose interchangeably with no difference in kinetics. Initial rate experiments weredone with larger volumes and higher sugar?metal ratios in orderto capture the low conversion data points. In order to determinethe initial rates at higher temperature ranges, an arabinose to Snratio of 1000 or 2000 was used. The thick-walled glass vials weresealed using a PTFE/silicone septa and metal crimp top, placed in atemperature-controlled oil bath, and removed periodically to takesamples. The glass reactors were quenched in ice and a small sam-ple volume was removed. Next, 100 l of the filtered sample and25 l of a 10 wtpercent mannitol solution were mixed in a vial. The sam-ples were analyzed by high-performance liquid chromatography(HPLC) on an Agilent 1260 system equipped with photodiode arrayultraviolet and evaporative light-scattering detectors. The reactionproducts were separated using a Bio-Rad Aminex HPX-87C columnheated to 353 K using deionized water (pH = 7) as the mobile phaseat a flow rate of 0.6 ml min?1. Ribulose concentrations were deter-mined using an ultraviolet detector at a wavelength 210 nm. At thiswavelength all other sugars had negligible ultraviolet signals. Forall ultraviolet-inactive carbohydrates, the analysis was performedusing the evaporative light scattering detector. Samples were runin duplicate on the HPLC and the column was regenerated dailywith 0.1 M Ca(NO3)2. Ketoses showed the strongest tendency toshift retention time in the column. Fractionation and NMR wereused to check peak purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid; In water; at 120℃; for 4h; | Compound 1 (about 4 mg) was added into a solution of water (1 mL) and 2N aqueous CF3COOH(2 mL), heated to 120°C under reflux conditions for 4 h. The mixture was diluted with water (2 mL) and then extracted with EtOAc (3 £2 mL). The combined organic phase was washed with brine and evaporated to dryness to afford the aglycones. The aqueous phase was concentrated. Then dry pyridine (1 mL) and L-cysteine methyl ester hydrochloride (2 mg) were added into the residue. Each mixture was reacted at 60°C for 1 h, and 0.5mL of (trimethylsilyl) imidazole dissolved in H2O was added, followed by heating to dryness at 60°C for 2 h. Each dried reactant was extracted with n-hexane (3 £ 1 mL) and H2O (1 mL, each). The n-hexane fraction was subjected to GC (column: Rtx-1, 0.25mm i.d. 0.25 mm, length 30 m). The conditions of GC were flame ionization detector; column temperature 100?180°C (10°C min?1)and 180?230°C (3°C min21); injector temperature 250°C; detector temperature 300°C and the carrier gas (N2, 0.8mLmin21). Under these conditions, these sugars of each reactants were identified by comparison with authentic samples: tR (min) 7.56 (D-ribose), 7.85 (L-ribose), 10.49 (D-glucose) and 11.10 (L-glucose). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; In acetic acid; ethyl acetate; | (1S,2S,3R)-1-(5-(trifluoromethyl)-1H-benzo[d]imidazole-2-yl)butane-1,2,3,4-tetraol D-/<strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (10 mg) and 4-trifluoromethanephenyldiamine (10 mg) with catalytic amount of iodine (1 mg) in acetic acid (1 mL) was reacted at room temperature for 12 hour. The resulting solution was precipitated by ethyl acetate (30 mL) and centrifuged for three times to remove the excess reagent. The pellet was lyophilized to give RibCF3BIM. The supporting data is given below. C12H13F3N2O4; yellow powder; 1H NMR (D2O, 600 MHz) delta 8.17 (1H, s, ArH), 7.94 (1H, d, J=8.3 Hz, ArH), 7.88 (1H, d, J=8.4 Hz, ArH), 5.53 (1H, s, H1), 4.18 (1H, s, H2), 3.85-3.72 (3H, m, H3, H4a, H4b); 13C NMR (D2O, 150 MHz) delta 155.6, 132.8, 130.3, 127.6 (q, JF-C=32.7 Hz), 124.7, 123.0 (d, JF-C=3.2 Hz), 114.8, 112.1 (d, JF-C=4.1 Hz), 72.8, 70.9, 67.5, 62.5; 19F NMR (D2O, 470 MHz) delta -62.27; MS (MALDI-TOF) calcd for C12H13F3N2O4: 306.083; found: m/z 307.093 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; In acetic acid; ethyl acetate; | (1S,2S,3R)-1-(5-chloro-1H-benzo[d]imidazole-2-yl)butane-1,2,3,4-tetraol D-/<strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (10 mg) and 4-chlorophenyldiamine (10 mg) with catalytic amount of iodine (1 mg) in acetic acid (1 mL) was reacted at room temperature for 12 hour. The resulting solution was precipitated by ethyl acetate (30 mL) and centrifuged for three times to remove the excess reagent. The pellet was lyophilized to give RibClBIM. The supporting data is given below. C11H13ClN2O4; black powder; [alpha]25D +60.3 (c 0.001, DMSO); 1H NMR (DMSO-d6, 600 MHz) delta 7.71 (1H, d, J=1.8 Hz, ArH), 7.66 (1H, d, J=8.6 Hz, ArH), 7.41 (1H, dd, J=8.6, 1.8 Hz, ArH), 5.14 (1H, d, J=4.5 Hz, H1), 3.87 (1H, dd, J=7.0, 4.5 Hz, H2), 3.58 (1H, dd, J=10.9, 3.5 Hz, H4a), 3.51 (1H, ddd, J=7.0, 6.0, 3.5 Hz, H3), 3.44 (1H, dd, J=10.9, 6.0 Hz, H4b); 13C NMR (DMSO-d6, 150 MHz) delta 156.8, 134.1, 132.1, 128.6, 124.6, 115.8, 114.1, 74.0, 71.8, 68.0, 62.9; MS (MALDI-TOF) calcd for C11H14ClN2O4: 273.056; found: m/z 272.990 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; In acetic acid; ethyl acetate; | (1S,2S,3R)-1-(5,6-dichloro-1H-benzo[d]imidazole-2-yl)butane-1,2,3,4-tetraol D-/<strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (10 mg) and 4,5-dichlorophenyldiamine (10 mg) with catalytic amount of iodine (1 mg) in acetic acid (1 mL) was reacted at room temperature for 12 hour. The resulting solution was precipitated by ethyl acetate (30 mL) and centrifuged for three times to remove the excess reagent. The pellet was lyophilized to give RibCl2BIM. The supporting data is given below. C11H12Cl2N2O4; black powder; mp=220-222° C.; [alpha]25D +23.3 (c 0.01, DMSO); 1H NMR (DMSO-d6, 600 MHz) delta 7.74 (1H, s, ArH), 5.01 (1H, d, J=4.4 Hz, H1), 3.82 (1H, dd, J=6.7, 4.4 Hz, H2), 3.55 (1H, dd, J=11.0, 3.5 Hz, H4a), 3.52 (1H, ddd, J=6.7, 5.8, 3.5 Hz, H3), 3.43 (1H, dd, J=11.0, 5.8 Hz, H4b); 13C NMR (DMSO-d6, 150 MHz) delta 158.8, 137.7 (2*), 123.7 (2*), 116.2 (2*), 74.7, 71.9, 69.1, 63.2; MS (MALDI-TOF) calcd for C11H13Cl2N2O4: 307.017; found: m/z 306.961 [M+H]+; calcd for C11H12Cl2N2O4Na: 329.017; found: m/z 328.951 [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; In acetic acid; ethyl acetate; | (1S,2S,3R)-1-(5-bromo-1H-benzo[d]imidazole-2-yl)butane-1,2,3,4-tetraol D-/<strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (10 mg) and 4-bromophenyldiamine (10 mg) with catalytic amount of iodine (1 mg) in acetic acid (1 mL) was reacted at room temperature for 12 hour. The resulting solution was precipitated by ethyl acetate (30 mL) and centrifuged for three times to remove the excess reagent. The pellet was lyophilized to give RibBrBIM. The supporting data is given below. C11H13BrN2O4; purple powder; mp=108-110° C.; [alpha]25D +40.0 (c 0.001, DMSO); 1H NMR (DMSO-d6, 600 MHz) delta 7.83 (1H, d, J=0.8 Hz, ArH), 7.62 (1H, d, J=8.6 Hz, ArH), 7.51 (1H, dd, J=8.6, 0.8 Hz, ArH), 5.14 (1H, d, J=4.4 Hz, H1), 3.87 (1H, dd, J=6.7, 4.4 Hz, H2), 3.58 (1H, dd, J=11.0, 3.5 Hz, H4a), 3.51 (1H, ddd, J=6.7, 5.8, 3.5 Hz, H3), 3.44 (1H, dd, J=11.0, 5.8 Hz, H4b); 13C NMR (DMSO-d6, 150 MHz) delta 156.6, 135.2, 132.9, 126.8, 117.0, 116.1, 116.0, 74.0, 71.8, 68.1, 62.9; MS (MALDI-TOF) calcd for C11H14BrN2O4: 317.006; found: m/z 316.946 [M+H]+; calcd for C11H13BrN2O4Na: 339.006; found: m/z 338.930 [M+Na]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; In acetic acid; ethyl acetate; | (1S,2S,3R)-1-(5,6-dibromo-1H-benzo[d]imidazole-2-yl)butane-1,2,3,4-tetraol D-/<strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (10 mg) and 4,5-dibromorophenyldiamine (10 mg) with catalytic amount of iodine (1 mg) in acetic acid (1 mL) was reacted at room temperature for 12 hour. The resulting solution was precipitated by ethyl acetate (30 mL) and centrifuged for three times to remove the excess reagent. The pellet was lyophilized to give RibBr2BIM. The supporting data is given below. C11H12Br2N2O4; black powder; mp=244-246° C.; [alpha]25D +2.3 (c 0.01, DMSO); 1H NMR (DMSO-d6, 600 MHz) delta 7.94 (1H, s, ArH), 5.07 (1H, d, J=4.4 Hz, H1), 3.82 (1H, dd, J=6.7, 4.4 Hz, H2), 3.55 (1H, dd, J=11.0, 3.5 Hz, H4a), 3.52 (1H, ddd, J=6.7, 5.8, 3.5 Hz, H3), 3.43 (1H, dd, J=11.0, 5.8 Hz, H4b); 13C NMR (DMSO-d6, 150 MHz) delta 158.9, 132.1 (2*), 119.9 (2*), 118.7 (2*), 74.7, 71.9, 69.1, 63.2; MS (MALDI-TOF) calcd for C11H13Br2N2O4: 394.916 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; In acetic acid; ethyl acetate; | (1S,2S,3R)-1-(5-fluoro-1H-benzo[d]imidazole-2-yl)butane-1,2,3,4-tetraol D-/<strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (10 mg) and 4-fluorophenyldiamine (10 mg) with catalytic amount of iodine (1 mg) in acetic acid (1 mL) was reacted at room temperature for 12 hour. The resulting solution was precipitated by ethyl acetate (30 mL) and centrifuged for three times to remove the excess reagent. The pellet was lyophilized to give RibFBIM. The supporting data is given below. C11H13FN2O4; black syrup; 1H NMR (D2O, 600 MHz) delta 7.78 (1H, dd, J=9.1, 4.5 Hz, ArH), 7.55 (1H, dd, J=8.2, 2.3 Hz, ArH), 7.39 (1H, td, J=9.4, 2.3 Hz, ArH), 5.47 (1H, d, J=4.5 Hz, H1), 4.13 (1H, dd, J=7.4, 4.4 Hz, H2), 3.79 (1H, dd, J=9.2, 5.0 Hz, H4a), 3.74-3.69 (2H, m, H3, H4b); 13C NMR (D2O, 150 MHz) delta 160.6 (d, JF-C=241.1 Hz), 153.9, 131.2 (d, JF-C=14.2 Hz), 127.3, 115.3 (d, JF-C=10.3 Hz), 114.8 (d, JF-C=26.1 Hz), 100.5 (d, JF-C=28.0 Hz), 72.8, 71.0, 67.4, 62.5; 19F NMR (MeOH-d4, 470 MHz) delta -115.8; HRMS (ESI) calcd for C11H13FN2O4: 256.086. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine; In acetic acid; ethyl acetate; | (1S,2S,3R)-1-(5,6-difluoro-1H-benzo[d]imidazole-2-yl)butane-1,2,3,4-tetraol D-/<strong>[24259-59-4]L-<strong>[24259-59-4]ribose</strong></strong> (10 mg) and 4,5-difluorophenyldiamine (10 mg) with catalytic amount of iodine (1 mg) in acetic acid (1 mL) was reacted at room temperature for 12 hour. The resulting solution was precipitated by ethyl acetate (30 mL) and centrifuged for three times to remove the excess reagent. The pellet was lyophilized to give RibF2BIM. The supporting data is given below. C11H12F2N2O4; brownish syrup; 1H NMR (D2O, 600 MHz) delta 7.74 (2H, t, J=7.7 Hz, ArH), 5.47 (1H, s, H1), 4.15 (1H, s, H2), 3.82 (1H, d, J=8.8 Hz, H3), 3.73 (2H, d, J=6.4 Hz, H4a, H4b); 13C NMR (MeOH-d4, 150 MHz) delta 158.3, 150.3 (d, JF-C=245.9 Hz), 150.2 (d, JF-C=246.8 Hz), 129.5 (2*), 103.7 (d, JF-C=6.7 Hz), 103.6 (d, JF-C=6.5 Hz), 75.2, 73.5, 69.7, 64.5; 19F NMR (D2O, 470 MHz) delta -139.1; MS (MALDI-TOF) calcd for C11H12F2N2O4: 274.077; found: m/z 274.932 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Reflux; | General procedure: A solution from each of 9a,b (10 mmol) and aldopentose /aldohexose (10 mmol) in a mixture of acetic anhydride, acetic acid (1 : 1) (50 mL) was stirred under reflux for 3?5 h (under TLC control). The mixture was then extracted with chloroform several times (150?200 mL). After removal of chloroform under reduced pressure the residue (the intermediates 10a?d, 12a?d) was followed up in the next step without identification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Reflux; | General procedure: A solution from each of 9a,b (10 mmol) and aldopentose /aldohexose (10 mmol) in a mixture of acetic anhydride, acetic acid (1 : 1) (50 mL) was stirred under reflux for 3?5 h (under TLC control). The mixture was then extracted with chloroform several times (150?200 mL). After removal of chloroform under reduced pressure the residue (the intermediates 10a?d, 12a?d) was followed up in the next step without identification. |
Precautionary Statements-General | |
Code | Phrase |
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Prevention | |
Code | Phrase |
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P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
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P282 | Wear cold insulating gloves/face shield/eye protection. |
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P285 | In case of inadequate ventilation wear respiratory protection. |
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Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
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P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
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P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
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P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
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P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
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P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
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P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
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P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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