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CAS No. : | 14152-97-7 | MDL No. : | MFCD00043085 |
Formula : | C15H19NO9S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WOWNQYXIQWQJRJ-UXXRCYHCSA-N |
M.W : | 389.38 | Pubchem ID : | 99462 |
Synonyms : |
|
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P280-P284-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313 | UN#: | 2811 |
Hazard Statements: | H302+H312+H332-H315-H319-H334 | Packing Group: | Ⅲ |
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 |
---|---|---|
95% | for 3h; Heating; | |
78% | In toluene Reflux; | Synthesis of per-O-acetyl glycosyl hydrazino carbothioamide General procedure: A solution of per-O-acetyl glycosyl isothiocyanate(1/4/6) and different aromatic hydrazide (2a-c) in toluene wasrefluxed on heating mental for 5-6 h. The reaction was monitoredby TLC. After completion of the reaction, the solvent wasevaporated in vacuum and the resultant sticky residue wastriturated with petroleum ether (60-80 C) to afford solid whichwas crystallized from aqueous ethanol (Scheme-II). |
With pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrazine hydrate In dichloromethane at 20℃; for 2h; | |
89% | With hydrazine hydrate | |
87% | With hydrazine hydrate In 1,4-dioxane for 0.666667h; |
85% | With hydrazine hydrate In ethanol for 1h; | 1 4.1.1 Synthesis of N-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazide (2) in absolute ethanol as solvent To a solution of 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate 1 (3.89 g, 10 mmol) in 25 mL of absolute ethanol, a solution of 85% hydrazine hydrate (10 mmol, 1.2 mL) in 10 mL of absolute ethanol was added dropwise slowly with stirring in 30 min so that the reaction temperature is below 10 °C. The white precipitate appeared immediately when several drops of hydrazine were added due to low solubility of this thiosemicarbazide in ethanol. The temperature of solution was maintained between 10 and 12 °C. The mixture was continuously stirred at 20 °C for 30 min. The solid product then was isolated by filtering with suction. The crude product was crystallized from 96% ethanol to yield 3.75 g of white product 2. Yield 85%, m.p. 156-158 °C; ref. [27] : 169-171 °C. FT-IR (KBr, cm-1): ν 3322, 3129 (νNH), 1752 (νC=O ester), 1355 (νC=S), 1242, 1043 (νCOC ester); 1H NMR (DMSO-d6) δ (ppm): 12.77 (s, 1H, NHb), 9.23 (s, 1H, NH), 8.17 (s, 1H, NH), 4.58 (s, 2H, NH2), 5.80 (m, 1H, H-1), 5.07 (t, J = 9.5 Hz, 1H, H-2), 5.34 (t, J = 9.75 Hz, 1H, H-3), 4.91 (t, J = 9.75 Hz, 1H, H-4), 4.14 (dd, J = 12.25, 4.75 Hz, 1H, H-6a), 3.98-3.93 (m, 2H, H-5 & H-6b), 1.98-1.94 (s, 12H, 4 * CH3CO); 13C NMR (DMSO-d6) δ (ppm): 182.1 (C=S), 169.9-169.2 (4 * COCH3), 81.0 (C-1), 70.5 (C-2), 72.5 (C-3), 68.1 (C-4), 72.1 (C-5), 61.8 (C-6), 20.4-20.2 (4 * CH3CO); MS (+ESI): m/z (%) = 422.42 (45) [M+H]+, 462.28 (100) [M+K]+; calcd. for C15H23N3O9S = 421.12 Da. |
With 1,4-dioxane; hydrazine hydrate | ||
With pyridine; hydrazine hydrate | ||
With hydrazine In ethanol at 5 - 10℃; Inert atmosphere; | ||
With hydrazine In ethanol Inert atmosphere; | ||
With hydrazine hydrate In dichloromethane | ||
With hydrazine In chloroform at 0 - 20℃; for 0.5h; | ||
With hydrazine hydrate In ethanol at 10 - 12℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In benzene Heating; or acetone; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | for 3h; Heating; | |
78% | In toluene Reflux; | Synthesis of per-O-acetyl glycosyl hydrazino carbothioamide General procedure: A solution of per-O-acetyl glycosyl isothiocyanate(1/4/6) and different aromatic hydrazide (2a-c) in toluene wasrefluxed on heating mental for 5-6 h. The reaction was monitoredby TLC. After completion of the reaction, the solvent wasevaporated in vacuum and the resultant sticky residue wastriturated with petroleum ether (60-80 C) to afford solid whichwas crystallized from aqueous ethanol (Scheme-II). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.21% | In benzene for 0.466667h; Microwave irradiation; | |
62% | In N,N-dimethyl-formamide at 50℃; for 8h; Inert atmosphere; | Synthesis of LC1 General procedure: Synthesis of L: 1-Aminoanthraquinone (220 mg, 10.8 mmol) was dissolved in dry DMF and a solution of 2, 3, 4, 6-O-acetyl-d-glucopyranosyl isothiocyanate (LP2) (375.5 mg 10.6 mmol) was added to this and stirred under N2 atmosphere at 50 °C for 8 hrs. The reaction mixture was cooled to room temperature. After removal of DMF under vacuum, the resulting brown residue was diluted with MeOH. Silica gel was added, and the mixture was evaporated to dryness. The dry powder was applied to silica gel 2:3 (EtOAc/Pet ether) to afford a light yellow product as powder Same procedure has been followed as that of L, aniline (90 mg, 10.8 mmol), 2, 3, 4, 6-O-acetyl-d-glucopyranosyl isothiocyanate (375.5 mg 10.6 mmol) to obtain the product in 62% yield as white powder. |
In benzene Heating; |
In benzene for 3h; Reflux; | Synthesis of N-phenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylthiocarbamide 0.02 M i.e. 7.8 g of 2,3,4,6-tetra-O-acetyl-β-D-glucopyronosyl isothiocyanate was dissolved in 50 mL benzene. In another flask solution of 1.8 g of aniline in 10 g of benzene was prepared. Both the solutions were mixed and allowed to reflux over boiling water bath for 3 h. After refluxing with said conditions benzene was removed by distillation. A sticky mass was obtained as residue, which was triturated several times with petroleum ether. A granular solid with yield of 6.5 g was obtained. The product was crystallized from aq. ethanol (m.p. 162 °C) (Scheme-VII). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In dichloromethane at 20℃; for 2h; | |
In benzene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tri-n-butyl-tin hydride In diethyl ether at 25℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With chlorine In chloroform at 0℃; | |
89% | With chlorine In chloroform at 0 - 5℃; | General Procedure for Synthesis of N-tetra-O-acetyl-β-D-glucopyranosylisocyano dichloride (3) The chlorine gas generated from (KMnO4, 5g and concentrated hydrochloric acid,35 mL) was passed through a chloroform solution (40 mL) of N-tetra-O-acetyl-β-dglucopyranosylisothiocyanate (10 g) maintaining a temperature 0-5 C. After additionof the chlorine gas has been completed, the yellow reaction mixture was subjected to vacuumdistillation. When a sticky mass was obtained, it was triturated with petroleum etherto give a creamy solid. It was dissolved in hot benzene and finally petroleum ether wasadded to a cold benzene solution to precipitate out N-tetra-O-acetyl-β-d-glucopyranosylisocyanodichloride as white solid.Molecular formula: C15H19Cl2NO9, Yield-9.8g, 89%, mp-122-124C (Lit.valaue20125 C). 1H NMR δ ppm (CDCl3): 5.30 (t, J = 9.5Hz, 1H, H1), 3.81-5.21 (m, 6H,H2-6),2.01-2.12 (m, 12 H, acetyl protons). |
With chlorine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With N-benzyl-N,N,N-triethylammonium chloride In benzene for 3.5h; Heating; | |
79.05% | Stage #1: potassium thioacyanate With tetrabutylammomium bromide In acetonitrile at 20℃; for 3h; Molecular sieve; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide In acetonitrile for 3h; Molecular sieve; Inert atmosphere; | 1.3; 2.3 3) Preparation of 1-isothiocyanato-2,3,4,6-O-acetyl-β-D-glucose: Potassium isothiocyanate(583mg, 6.0mmol) in Tetrabutylammonium bromide (967mg, 3.0mmol),4A molecular sieve (4.5g) and 140mL anhydrous acetonitrile were stirred at room temperature under nitrogen for 3 hours,A solution of 1-bromo-2,3,4,6-O-acetyl-α-D-glucose (1233.6 mg, 1.0 mmol) in 10 mL of anhydrous acetonitrile was added to the above solution, and the reaction was heated for 3 hours. Cool to room temperature,Filtration, the filtrate was evaporated to dryness under reduced pressure,Column chromatography to obtain a white foamy solid, which is 1-isothiocyanato-2,3,4,6-O-acetyl-β-D-glucose (0.9234g, 79.05%); |
78% | In benzene for 3.5h; Heating; |
71% | With 4 A molecular sieve In acetonitrile 1.) room temp., 3 h, 2.) reflux, 3 h; | |
60% | In melt at 190℃; for 0.0833333h; | |
53% | With tetra-(n-butyl)ammonium iodide In acetonitrile for 3h; Molecular sieve; Reflux; | |
With tetrabutylammomium bromide In acetonitrile at 82℃; for 2h; Molecular sieve; | ||
Inert atmosphere; | ||
With tetrabutylammomium bromide In acetonitrile for 4h; Reflux; | ||
at 190℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In benzene for 6h; Heating; | |
89.66% | In 5,5-dimethyl-1,3-cyclohexadiene at 130 - 140℃; for 0.416667h; Microwave irradiation; | |
89% | In toluene for 4h; Reflux; | 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate(7) A solution of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylbromide 6 (12 mmol) in toluene (20 mL) was added dropwise in a gently refluxing mixture of lead thiocyanate (15mmol) and toluene (30 mL). The mixture was refluxed withmechanical stirring for 4 h, and the resulting solid (lead salt)was filtered from this hot mixture and washed with hot toluene(15 mL). Petroleum ether (30 ~ 60 °C) was then added tothe filtrate, after cooling the pure crystalline product (7) wasseparated as a white solid. Yield 89%, mp 111-113 °C, lit.[22] mp 110-112°C. |
3.5 g | In xylene for 3h; Heating; | |
for 8h; Reflux; | ||
In o-xylene at 145℃; for 8h; | ||
for 8h; boiling; | ||
In 5,5-dimethyl-1,3-cyclohexadiene for 3h; Reflux; | ||
In 5,5-dimethyl-1,3-cyclohexadiene for 3h; Reflux; | Synthesis of 2,3,4,6-tetra-O-acetyl β-D-glucopyranosylisothiocyanate A solution of 20 g of tetra-O-acetyl-α-D-glucopyranosyl-bromide in 150 mL xylene was prepared.To this solution 16 g of lead isothiocyanate was added. The-reaction mixture was refluxed for 3 h with frequent shaking.The solution was allowed to cool and separated out by filtration-from lead bromide [9,17]. The xylene filtrate was added to petroleum ether result into solid product with yield of 14 g.The product was purified by dissolving it in minimum quantity of ethanol and re-precipitated by water. The product was confirmedby melting point (112-114 °C) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | In toluene at 80℃; for 0.5h; Microwave irradiation; | |
55% | With triethylamine In benzene for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In pyridine; water at 20℃; for 24h; | |
With 4-nitro-phenol; triethylamine In benzene Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With triethylamine Ambient temperature; | |
93% | With pyridine at 20℃; for 24h; | |
93% | With pyridine; triethylamine at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With triphenylphosphine In toluene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With triphenylphosphine In toluene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triphenylphosphine In toluene at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With silver trifluoroacetate; triethylamine In acetonitrile at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With silver trifluoroacetate; triethylamine In acetonitrile at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With silver trifluoroacetate; triethylamine In acetonitrile at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With silver trifluoroacetate; triethylamine In acetonitrile at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In pyridine at 20℃; for 2h; | |
90% | With pyridine at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With thiamine diphosphate In toluene at 20℃; for 24h; | |
With thiamine diphosphate In toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With silver trifluoroacetate; triethylamine In acetonitrile at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With silver trifluoroacetate; triethylamine In acetonitrile at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With silver trifluoroacetate; triethylamine In acetonitrile at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With silver trifluoroacetate; triethylamine In acetonitrile at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With silver trifluoroacetate; triethylamine In acetonitrile at 50℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In dichloromethane at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With sodium hydrogencarbonate In water; acetone at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With sodium hydrogencarbonate In water; acetone at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With triphenylphosphine In toluene at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With triphenylphosphine In toluene at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triphenylphosphine In toluene at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With thiamine diphosphate In toluene at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In toluene at 20℃; for 24h; | |
With triphenylphosphine In toluene at 80℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 84% 2: 72% | With triethylamine In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With triphenylphosphine In toluene at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With sodium hydrogencarbonate In water; acetone at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With thiamine diphosphate In toluene at 20℃; for 18h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With pyridine at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With pyridine at 20℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With pyridine at 20℃; for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With pyridine at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With tin(IV) chloride In dichloromethane at 20℃; for 48h; | |
With tin(IV) chloride In dichloromethane at 30℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | In dichloromethane at 20℃; | |
45% | In dichloromethane at 0℃; for 0.5h; | |
In dichloromethane at 20℃; |
In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In dichloromethane at 20℃; | |
47% | In dichloromethane at 0℃; for 0.5h; | |
In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With triethylamine In dichloromethane at 20℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With calcium carbonate In dichloromethane; water at 25℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With triethylamine In dichloromethane at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With triethylamine In dichloromethane at 20℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With ammonia In toluene at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In dichloromethane at 20℃; Inert atmosphere; | |
79% | In dichloromethane at 20℃; Inert atmosphere; | |
50% | In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With triethylamine In dichloromethane at 0 - 20℃; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In tetrahydrofuran at 35℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In dichloromethane at 20℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With triphenylphosphine In toluene at 80℃; for 2h; Inert atmosphere; | 4.5. General procedure for the preparation of 3-O-acetyl-5-alkyl (aryl, glycopyranosyl)carbodiimido-5-deoxy-1,2-O-isopropylidene-6-O-trimethylsilyl-α-d-furanoses via aza-Wittig reaction (19, 21, 23, 27 and 29) General procedure: A solution of azide 18 or 26 (186 mg, 0.52 mmol) in toluene (3.5 mL) was stirred under Ar for 30 min. Then, the corresponding phenyl, naphtyl, or 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate (0.62 mmol) and a solution of PPh3 (0.63 mmol) in toluene (2 mL) were added at room temperature. The reaction mixture was stirred at 80 °C for 2 h and concentrated. The resulting residue was purified by column chromatography using the eluent indicated in each case to afford the carbodiimide derivatives 19, 21, 23, 27 and 29 as amorphous solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With triphenylphosphine In toluene at 80℃; for 2h; Inert atmosphere; | 4.5. General procedure for the preparation of 3-O-acetyl-5-alkyl (aryl, glycopyranosyl)carbodiimido-5-deoxy-1,2-O-isopropylidene-6-O-trimethylsilyl-α-d-furanoses via aza-Wittig reaction (19, 21, 23, 27 and 29) General procedure: A solution of azide 18 or 26 (186 mg, 0.52 mmol) in toluene (3.5 mL) was stirred under Ar for 30 min. Then, the corresponding phenyl, naphtyl, or 2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate (0.62 mmol) and a solution of PPh3 (0.63 mmol) in toluene (2 mL) were added at room temperature. The reaction mixture was stirred at 80 °C for 2 h and concentrated. The resulting residue was purified by column chromatography using the eluent indicated in each case to afford the carbodiimide derivatives 19, 21, 23, 27 and 29 as amorphous solids. |