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Product Details of [ 70741-39-8 ]

CAS No. :70741-39-8 MDL No. :MFCD22193860
Formula : C8H11NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :DYMYLBQTHCJHOQ-UHFFFAOYSA-N
M.W : 185.18 Pubchem ID :575321
Synonyms :

Safety of [ 70741-39-8 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 70741-39-8 ]

* 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.

  • Downstream synthetic route of [ 70741-39-8 ]

[ 70741-39-8 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 70741-39-8 ]
  • [ 76494-20-7 ]
  • [ 76398-89-5 ]
YieldReaction ConditionsOperation in experiment
64% In 1,4-dioxane for 72h; Ambient temperature;
YieldReaction ConditionsOperation in experiment
47% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 21h; 2 General Procedure for Acid-NHS Ester Preparations General procedure: N-Hydroxysuccinimide (0.62 g, 0.0053 mol, 1.0 equiv.) followed by EDC (0.00795 mmol, 1.5 equiv.) was added to a solution of the respective acid (0.0053 mol, 1.0 equiv) in anhydrous THF (13 mL). The solution was stirred for 21 h at room temperature. The solvent was evaporated in vacuum and the resulting residue dissolved in ethylacetate (80 mL). The organic phase was washed with saturated NaHCO3 (2×20 mL) and NaCl solution (2×20 mL), dried with NaSO4, and filtered. The solvent was removed under vacuum to give crude NHS ester. The crude product was recrystallized with ethylacetate/petroleum ether to obtain the desired NHS esters below. The esters were used for coupling without any further purification. 1H and 13C NMR indicated relatively clean esters (see below).
entspr. Saeurechlorid, Thallium-N-hydroxysuccinimid;
Buttersaeure, N-Hydroxysuccinimid, Dicyclohexylcarbodiimid;
  • 3
  • [ 70741-39-8 ]
  • [ 2152-75-2 ]
  • [ 884856-17-1 ]
YieldReaction ConditionsOperation in experiment
86% With potassium hydroxide In tetrahydrofuran; water at 20℃;
  • 4
  • [ 70741-39-8 ]
  • (1S,3R,4S,5R,6R,7S)-4,5-dihydroxy-3-(hydroxymethyl)-2-oxabicyclo[4.1.0]heptan-7-aminium trifluoroacetate [ No CAS ]
  • [ 1202246-30-7 ]
YieldReaction ConditionsOperation in experiment
63% With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;
  • 5
  • [ 6066-82-6 ]
  • [ 107-92-6 ]
  • [ 70741-39-8 ]
YieldReaction ConditionsOperation in experiment
63% With dicyclohexyl-carbodiimide In acetonitrile at 20℃; for 18h;
47% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 21h;
30% With dicyclohexyl-carbodiimide In acetonitrile at 20℃; for 18h; General procedure: Prepared as described for crotonicacid NHS ester. Viscous yellowoil (125 mg, 30%). 1H NMR (600 MHz,methanol-d4) dH 2.83 (4H, s, 2NCOCH2), 2.60 (2H, t, J 7.5 Hz,CH2CO), 1.78e1.72 (2H, m, CH3CH2), 1.04 (3H, t, J 7.5 Hz, CH3).
With dicyclohexyl-carbodiimide In 1,4-dioxane at 20℃; for 1h; 258 35 mg of butanoic acid was dissolved in 0.5 mL of 1,4-dioxane, to which 46 mg of N-hydroxysuccinimide and 82 mg of N,N'-dicyclohexylcarbodiimide were added, and stirred at room temperature for 1 hour. The deposit was filtered off, and the solvent was evaporated to obtain 94 mg of butanoic acid 2,5-dioxopyrrolidin-1-yl ester crude product. The crude product was used in the next reaction without further purification.
With dicyclohexyl-carbodiimide In dichloromethane at 6℃; for 20h;
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 25℃; for 14h; Inert atmosphere;
With dicyclohexyl-carbodiimide In ethyl acetate at 20℃;
With dicyclohexyl-carbodiimide In dichloromethane at 0 - 23℃; for 16h; Inert atmosphere; 4.1.1. General procedure for synthesis of NHS esters (method A) General procedure: To a solution of the appropriate fatty acid 9b, 13b-37b (1.0equiv) in CH2Cl2 (0.1 M) at 0°C was added N-hydroxysuccinimide (NHS, 1.0 equiv) and N,N'-dicyclohexylcarbodiimide (1.0 equiv). The reaction mixture was warmed to 23°C and stirred 16 h. Theresulting mixture was filtered and the filtrate was concentrated under reduced pressure to provide NHS esters 9c, 13c-37c without further purification.

  • 6
  • [ 70741-39-8 ]
  • [ 3105-95-1 ]
  • N-butanoyl L-pipecolic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With potassium carbonate In tetrahydrofuran Reflux;
  • 7
  • [ 70741-39-8 ]
  • [ 1227864-55-2 ]
  • [ 1227865-01-1 ]
YieldReaction ConditionsOperation in experiment
In ethanol at 20℃; for 48h; 258 30 mg of 4-(benzylamino)-6-[4-piperazin-1-yl]phenyl}amino)pyridine-3-carboxyamide (the compound of Example 219) was dissolved in 4 mL of ethanol, to which 21 mg of butanoic acid 2,5-dioxopyrrolidin-1-yl ester and 15 mg of triethylamine were added, and stirred at room temperature for 2 days. The solvent was evaporated, and the residue was dissolved in chloroform, washed with saturated sodium bicarbonate in water and saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=7:1) to obtain 27 mg (77%) the title compound as a light yellow solid.m.p. 233.5-235.2° C. (dec.)1H-NMR (400 MHz, CDCl3) δ: 1.00 (3H, t, J=7.4 Hz), 1.66-1.76 (2H, m), 2.37 (2H, t, J=7.7 Hz), 3.09-3.16 (4H, m), 3.63-3.67 (2H, m), 3.76-3.82 (2H, m), 4.31 (2H, d, J=5.5 Hz), 5.58 (2H, br), 5.75 (1H, s), 6.48 (1H, brs), 6.81 (2H, d, J=8.8 Hz), 6.94 (2H, d, J=8.8 Hz), 7.24-7.36 (5H, m), 8.20 (1H, s), 8.89 (1H, brt, J=5.5 Hz).IR (ATR): 1653, 1619, 1556, 1518, 1409, 1226, 1158, 1027 cm-1.MS: m/z 472 (M+, base peak).
  • 8
  • [ 70741-39-8 ]
  • [ 104566-44-1 ]
  • [ 1354638-34-8 ]
YieldReaction ConditionsOperation in experiment
1.4 g With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 20h;
  • 10
  • [ 70741-39-8 ]
  • pentyl (sodium 3-O-methyl-2-O-sodium sulphonato-α-L-idopyranosyluronate)-(1->4)-(2-amino-2-deoxy-3-O-methyl-6-O-sodium sulphonato-α-D-glucopyranosyl)-(1->4)-(sodium 3-O-methyl-2-O-sodium sulphonato-α-L-idopyranosyluronate)-(1->4)-(2-amino-2-deoxy-3-O-methyl-6-O-sodium sulphonato-α-D-glucopyranosyl)-(1->4)-(sodium 3-O-methyl-2-O-sodium sulphonato-α-L-idopyranosyluronate)-(1->4)-(2-amino-2-deoxy-3-O-methyl-6-O-sodium sulphonato-α-D-glucopyranosyl)-(1->4)-(sodium 3-O-methyl-2-O-sodium sulphonato-α-L-idopyranosyluronate)-(1->4)-2-amino-2-deoxy-3-O-methyl-6-O-sodium sulphonato-β-D-glucopyranoside [ No CAS ]
  • pentyl (sodium 3-O-methyl-2-O-sodium sulphonato-α-L-idopyranosyluronate)-(1->4)-(2-butanoylamino-2-deoxy-3-O-methyl-6-O-sodium sulphonato-α-D-glucopyranosyl)-(1->4)-bis[(sodium 3-O-methyl-2-O-sodium sulphonato-α-L-idopyranosyluronate)-(1->4)-(2-butanoylamino-2-deoxy-3-O-methyl-6-O-sodium sulphonato-α-D-glucopyranosyl)-(1->4)]-(sodium 3-O-methyl-2-O-sodium sulphonato-α-L-idopyranosyluronate)-(1->4)-2-butanoylamino-2-deoxy-3-O-methyl-6-O-sodium sulphonato-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 0 - 20℃; for 26.5h; Inert atmosphere; 3 EXAMPLE 3: Pentyl (sodium 3-0-methyl-2-0-sodium sulphonato-g-L- idopyranosyluronate)-(1 ^4)-(2-butanoylamino-2-deoxy-3-0-methyl-6-0-sodiumsulphonato-g-D-glucopyranosyl)-(1→4)-[(sodium 3-Q-methyl-2-0-sodium sulphonato-g-L- idopyranosyluronate)-(1 ^4)-(2-butanoylamino-2-deoxy-3-0-methyl-6-0-sodium sulphonato-g-D-glucopyranosvD-d→4)1?-(sodium 3-0-methyl-2-0-sodium sulphonato-g-L- idopyranosyluronate)-(1→4)-2-butanoylamino-2-deoxy-3-0-methyl-6-0-sodiumsulphonato-B-D-glucopyranoside (compound No. 3)A solution of Λ/,/V-diisopropylethylamine (1 1 μΙ, 0.063 mmol) in Λ/,/V-dimethyl- formamide (33 μΙ) and /V-butyroxysuccinimide (9 mg, 0.048 mmol), prepared according to Naito et al. Journal of Antibiotics, 29; 1976, 1286, dissolved in Λ/,/V-dimethylformamide (33 μΙ), are added, at 0°C under an argon atmosphere, to compound 53 (8.9 mg,0.00363 mmol) dissolved in Λ/,/V-dimethylformamide (471 μΙ) and water (290 μΙ). After magnetic stirring at ambient temperature for 3.5 h, two further additions of reagents are carried out (same amounts), 3 h 30 min apart. After stirring at ambient temperature for 16 h, the reaction medium is loaded onto a Sephadex G25-fine gel column (95 χ 2 cm) eluted with a 0.2 M aqueous solution of NaCI. The fractions containing the expected compound are combined, and loaded onto a Sephadex G25-fine gel column (95 χ 2 cm) eluted with water. The mixture obtained is reacted under the same conditions, to give 10.3 mg of compound 3.1H NMR [500 MHz] (D20) δ of the anomeric protons Glc' β: 4.45 ppm, IdoUA": 5.06 ppm, Glc'" a: 4.98 ppm, ldoUAlv: 5.06 ppm, Glcv a: 4.98 ppm, ldoUAvl: 5.06 ppm, Glcv" a: 4.98 ppm and ldoUAvl": 5.05 ppm.ESI-MS m/z 588.06 [(M - 4H)4"].
  • 11
  • [ 70741-39-8 ]
  • pentyl (sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-amino-2-deoxy-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyl uronate)-(1-4)-(2-amino-2-deoxy-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-amino-2-deoxy-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyl uronate)-(1-4)-2-amino-2-deoxy-6-O-sodium sulfonato-β-D-glucopyranoside [ No CAS ]
  • pentyl (sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-deoxy-2-(1-oxobutyl)-amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-αβ-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 0 - 20℃; for 18h; Example 2Pentyl (sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1→4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-(1-oxobutyl)-amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1→4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-αβ-glucopyranosyl)-(1→4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-β-D-glucopyranoside (Compound 2) To a solution of compound 43 (26 mg, 11.1 μmol) in a 7/3 mixture of N,N-dimethylformamide/water (2.9 mL) are added dropwise, at 0° C., diisopropylethylamine (33 μL, 17 molar equivalents) dissolved in N,N-dimethylformamide (100 μL) and N-hydroxysuccinimide butyrate (27.4 mg, 13 molar equivalents) dissolved in N,N-dimethylformamide (100 μL). Stirring is continued at room temperature for 4 hours, and the same amount of reagent is then added twice more under the same conditions. After a total of 18 hours of stirring at room temperature, the reaction medium is applied to a Sephadex G-25 column eluted with 0.2 M sodium chloride. The fractions containing the product are concentrated and desalified using the same column eluted with water. The fractions containing the product are then concentrated under high vacuum to give the desired compound 2 (26 mg, 89%).Chemical shifts of the anomeric protons (600 MHz, D2O) δ 5.14 IdoUAVIII, 5.12* GlcVII, 5.14 IdoUAVI, 5.11* GlcV, 5.14 IdoUAIV, 5.10* GlcIII, 5.15 IdoUAII, 4.50 GlcI *: The signals may be interchanged.“ESI” method, negative mode: multicharged ion detected m/z 588.1095 [M-4H]4- (acid form).
  • 12
  • [ 70741-39-8 ]
  • 5-phenylpentyl (sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-amino-2-deoxy-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-amino-2-deoxy-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-amino-2-deoxy-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-2-amino-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • 5-phenylpentyl (sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-deoxy-2-(1-oxobutyl)amino-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-2-deoxy-2-(1-oxobutyl)amino-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 0 - 20℃; for 26h; Example 145-phenylpentyl (sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1→4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1→4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-(1-oxobutyl)amino-α-D-glucopyranosyl)-(1→4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-2-deoxy-2-(1-oxobutyl)amino-β-D-glucopyranoside (Compound 14) To a solution of compound 171 (126 mg, 56.9 μmol) in a 7/3 mixture of N,N-dimethylformamide/water (12.6 mL) are added dropwise, at 0° C., diisopropylethylamine (148 μL, 14.9 molar equivalents) dissolved in N,N-dimethylformamide (100 μL), and N-hydroxysuccinimide butyrate (116 mg, 11 molar equivalents) dissolved in N,N-dimethylformamide (100 μL). Stirring is continued at room temperature for 3 hours, and the same amount of reagent is then added three times under the same conditions. After a total of 23 hours of stirring at room temperature, the reaction medium is applied to a Sephadex G-25 column eluted with 0.2 M sodium chloride. The fractions containing the product are concentrated and desalified using the same column eluted with water. The fractions containing the product are then concentrated under high vacuum to give the desired compound 14 (133 mg, 93%).Chemical shifts of the anomeric protons (600 MHz, D2O) δ 5.07 IdoUAVIII, 4.99 GlcVII, 5.09 IdoUAVI, 5.04 GlcV, 5.10 IdoUAIV, 5.01 GlcIII, 5.06 IdoUAII, 4.38 GlcI [α]D 50.5° (c 1; H2O).
  • 13
  • [ 70741-39-8 ]
  • 3,3-diphenylpentyl (sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-amino-2-deoxy-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-amino-2-deoxy-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-amino-2-deoxy-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-2-amino-2-deoxy-β-D-glucopyranoside [ No CAS ]
  • 3,3-diphenylpropyl (sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-(2-deoxy-2-(1-oxobutyl)-amino-α-D-glucopyranosyl)-(1-4)-(sodium-2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1-4)-2-deoxy-2-(1-oxobutyl)amino-β-D-glucopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 0 - 20℃; for 27h; Example 183,3-diphenylpropyl (sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1→4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-(1-oxobutyl)amino-6-O-sodium sulfonato-α-D-glucopyranosyl)-(1→4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-(2-deoxy-2-(1-oxobutyl)-amino-α-D-glucopyranosyl)-(1→4)-(sodium 2-O-sodium sulfonato-α-L-idopyranosyluronate)-(1→4)-2-deoxy-2-(1-oxobutyl)amino-β-D-glucopyranoside (Compound 18) To a solution of compound 174 (5.5 mg, 2.4 μmol) in a 2/1 mixture of N,N-dimethylformamide/water (4.8 mL) are added dropwise, at 0° C., diisopropylethylamine (63 μL, 15 molar equivalents) dissolved in N,N-dimethylformamide (43 μL), and N-hydroxysuccinimide butyrate (49 mg, 11 molar equivalents) dissolved in N,N-dimethylformamide (43 μL). Stirring is continued at room temperature for 3 hours, and the same amount of reagent is then added three times under the same conditions. After a total of 24 hours of stirring at room temperature, the reaction medium is applied to a Sephadex G-25 column eluted with 0.2 M sodium chloride. The fractions containing the product are concentrated and desalified using the same column eluted with water. The fractions containing the product are then concentrated under high vacuum to give the desired compound 18 (6 mg, 98%).Chemical shifts of the anomeric protons (600 MHz, D2O) δ 5.22 IdoUAVIII, 5.19 GlcVII, 5.23 IdoUAVI, 5.13 GlcV, 5.23 IdoUAIV, 5.17 GlcIII, 5.20 IdoUAII, 4.48 GlcI [α]D +24° (c 0.48, H2O).
  • 14
  • [ 70741-39-8 ]
  • [ 147-85-3 ]
  • [ 23500-13-2 ]
YieldReaction ConditionsOperation in experiment
25% With potassium carbonate In tetrahydrofuran for 5h; Reflux; 4 General procedure: 3.10.4 N-Butanoyl-l-proline 22 Prepared as described for N-crotonyl-l-proline. Colorless oil (tR=9.7 min; 4.0 mg, 25%); [α]D22 -45 (c 0.10, MeOH); 1H NMR (600 MHz, methanol-d4) δH trans rotamer 4.24 (1H, dd, J 8.7, 3.3 Hz, NCHCO2H), 3.64-3.60 (1H, m, NCH2), 3.51-3.45 (1H, m, NCH2), 2.36-2.31 (1H, m, COCH2), 2.29-2.20 (1H, m, NCHCH2), 2.27-2.22 (1H, m, COCH2), 2.15-2.10 (1H, m, NCHCH2), 1.97-1.89 (1H, m, NCHCH2), 1.86-1.80 (1H, m, NCH2CH2), 1.69-1.58 (2H, m, CH3CH2), 0.94 (3H, t, J 7.6 Hz, CH3). δH cis rotamer 4.32 (1H, dd, J 8.7, 3.8 Hz, NCHCO2H), 3.69-3.65 (1H, m, NCH2), 3.54-3.50 (1H, m, NCH2), 2.36-2.32 (1H, m, NCH2CH2), 2.27-2.22 (1H, m, COCH2), 2.16-2.11 (1H, m, NCHCH2), 2.05-2.00 (1H, m, CH2CH2), 2.02-1.98 (1H, m, NCHCH2), 1.93-1.89 (1H, m, NCH2CH2), 1.69-1.58 (2H, m, CH3CH2), 0.97 (3H, t, J 7.6 Hz, CH3); 13C NMR (150 MHz, methanol-d4) δC trans rotamer 180.0, 174.7, 63.8, 47.5, 37.3, 32.7, 23.9, 19.3, 14.2. δC cis rotamer 179.6, 173.8, 62.7, 48.4, 37.3, 31.1, 25.5, 19.3, 14.2. HRESI(+)MS m/z 208.0944 (calcd for C9H15NNaO3, 208.0950).
  • 15
  • [ 70741-39-8 ]
  • C13H18N6O7S*1.5C6H15N [ No CAS ]
  • [ 121-44-8 ]
  • C17H24N6O8S*1.2C6H15N [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 2,5-dioxopyrrolidin-1-yl butyrate; C13H18N6O7S*1.5C6H15N With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20℃; Cooling with ice; Stage #2: triethylamine In water; acetonitrile
  • 16
  • 2-deoxy-2-amino glucose [ No CAS ]
  • [ 70741-39-8 ]
  • N-(2,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-3-yl)butyramide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With triethylamine In methanol at 20℃; for 6h;
  • 17
  • [ 70741-39-8 ]
  • [ 112921-00-3 ]
  • [ 121-44-8 ]
  • 5'-O-[N-(butanoyl)sulfamoyl]-2',3'-O-isopropylideneadenosine triethylammonium [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: 2,5-dioxopyrrolidin-1-yl butyrate; ((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate With caesium carbonate In N,N-dimethyl-formamide at 0 - 23℃; for 16h; Inert atmosphere; Stage #2: triethylamine In methanol; ethyl acetate 4.1.3. General procedure for acylation General procedure: To a solution of 5'-O-sulfamoyl-20,30-O-isopropylideneadenosine (1.0 equiv) in anhydrous DMF (0.1 M) at 0 Cwere added cesium carbonate (3.0 equiv) and the appropriate N-hydroxysuccinimylester 9c, 13c-56c (1.5 equiv). The mixture was warmed to 23°C and stirred for 16 h. The resulting mixture was filtered and the filtrate was concentrated under reduced pressure. Purification by flash chromatography (0-20% EtOAc/MeOH 0.5%Et3N) afforded the title compounds 9d, 13d-56d as colorless oils.
  • 18
  • [ 6066-82-6 ]
  • [ 123-72-8 ]
  • [ 70741-39-8 ]
YieldReaction ConditionsOperation in experiment
72% With tert.-butylhydroperoxide; sodium hydride; 1,3-bis(mesityl)imidazolium chloride In acetonitrile; mineral oil for 8h; Inert atmosphere; Schlenk technique;
  • 19
  • [ 70741-39-8 ]
  • [ 100-46-9 ]
  • [ 10264-14-9 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 20℃; Schlenk technique; Inert atmosphere;
  • 20
  • [ 70741-39-8 ]
  • C26H35N3O5 [ No CAS ]
  • C30H41N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;
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