[ CAS No. 35717-98-7 ] {[proInfo.proName]}

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Quality Control of [ 35717-98-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 35717-98-7 ]

SDS Specification

Alternatived Products of [ 35717-98-7 ]

Product Details of [ 35717-98-7 ]

CAS No. :	35717-98-7	MDL No. :	MFCD06660915
Formula :	C₁₄H₂₃O₆PS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	350.37	Pubchem ID :	-
Synonyms :

Safety of [ 35717-98-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 35717-98-7 ]

* 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 [ 35717-98-7 ]

[ 35717-98-7 ] Synthesis Path-Downstream 1~13

1
[ 156-81-0 ]
[ 35717-98-7 ]
2,4-diamino-1-(diisopropoxy-phosphorylmethyl)-pyrimidin-1-ium; toluene-4-sulfonate [ No CAS ]

Reference： [1]Acta Crystallographica Section B: Structural Science,2002,vol. 58,p. 519 - 529

2
[ 5754-34-7 ]
[ 35717-98-7 ]
[ 918795-56-9 ]

Reference： [1]Nucleosides, nucleotides and nucleic acids,2006,vol. 25,p. 121 - 140

3
[ 14690-00-7 ]
[ 35717-98-7 ]
[ 927814-91-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 2-O-benzylglycerol With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate In N,N-dimethyl-formamide at 20℃; for 8h;

Reference： [1]Vrbovska, Silvie; Holy, Antonin; Pohl, Radek; Masojidkova, Milena [Collection of Czechoslovak Chemical Communications, 2006, vol. 71, # 4, p. 543 - 566]

4
petroleum [ No CAS ]
triethylammonium hydrogen Carbonate [ No CAS ]
[ 691-96-3 ]
[ 98-59-9 ]
[ 35717-98-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; paraformaldehyde In chloroform; acetonitrile; benzene	Di(2-propyl) p-toluenesulphonyloxymethylphosphonate Di(2-propyl) p-toluenesulphonyloxymethylphosphonate Triethylamine (8.4 ml) is added to a stirred mixture of di(2-propyl)phosphite (96g) and paraformaldehyde (23g), and the mixture is heated to 100°C (reflux condenser, calcium chloride protecting group) until the paraformaldehyde dissolves completely. After heating for one more hour, the reaction mixture is cooled and mixed with acetonitrile (500 ml) and p-toluenesulphonyl chloride (121.5g). Triethylamine (90 ml) and 4-dimethylaminopyridine are then added under stirring. After stirring for 24hrs the mixture is cooled with ice, 0.4 M triethylammonium hydrogen carbonate (400 ml) is gradually added and the mixture is again stirred for 24hrs. Acetonitrile is evaporated in vacuo (bath temperature below 40°C) and the mixture is extracted with ether (3 x 200 ml). The ethereal extract is dried over sodium sulphate, filtered, and the solvent is evaporated in vacuo . The residue is dissolved in benzene (200 ml) and filtered through a column of silica gel (500 ml, prepared in benzene). The column is washed with benzene until impurities of higher RFare removed (monitoring by TLC on silica gel plates in chloroform) and then the product is eluted with ethyl acetate. After evaporation of the solvent in vacuo , the remaining oil is stirred with light petroleum (300 ml) to crystallisation, the crystals are collected, washed with light petroleum and dried in vacuo . Yield 140 g of di(2-propyl) p-toluenesulphonyl-oxymethylphosphonate, m.p. 37.5°C. For C14H23PO6S (350.4) calculated: 47.98% C, 6.61% H, 8.86% P, 9.15% S; found: 48.15% C, 6.80% H, 9.02% P; 9.24% S.

Reference： [1]Current Patent Assignee: CZECH ACADEMY OF SCIENCES; KATHOLIEKE UNIVERSITEIT LEUVEN - EP454427, 1991, A1

5
[ 35717-98-7 ]
[ 52980-28-6 ]
[ 1389323-19-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;	1.1. General procedures for the syntheses of ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k General procedure: The appropriate oxoquinoline derivative 5 (1.75 mmol) was stirred for 15 minutes in the presence of 750.0 mg of K2CO3 and 5.0mL of DMF, followed by the addition of diisopropyl(tosylmethoxy)phosphonate 4 (3.50 mmol). The reaction mixture was additionally stirred for 48 h at 80 °C. Afterwards, the resulting mixture was poured into water (30 mL) and extracted with methylene chloride (3 x 20 mL). The combined organic extracts were washed with water (3 x 20 mL), dried over anhydrous magnesium sulfate, filtered and evaporated, giving rise to ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k which were purified by crystallization from ethyl ether.

Reference： [1]Faro, Leticia V.; De Almeida, Jessica M.; Cirne-Santos, Claudio C.; Giongo, Viveca A.; Castello-Branco, Luis R.; Oliveira, Ingrid De B.; Barbosa, Juliana E.F.; Cunha, Anna C.; Ferreira, Vitor F.; De Souza, Marcos C.; Paixao, Izabel C.N.P.; De Souza, Maria Cecilia B.V. [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 15, p. 5055 - 5058]

6
[ 35717-98-7 ]
[ 69994-70-3 ]
[ 1389323-29-8 ]

Yield	Reaction Conditions	Operation in experiment
29%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;	1.1. General procedures for the syntheses of ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k General procedure: The appropriate oxoquinoline derivative 5 (1.75 mmol) was stirred for 15 minutes in the presence of 750.0 mg of K2CO3 and 5.0mL of DMF, followed by the addition of diisopropyl(tosylmethoxy)phosphonate 4 (3.50 mmol). The reaction mixture was additionally stirred for 48 h at 80 °C. Afterwards, the resulting mixture was poured into water (30 mL) and extracted with methylene chloride (3 x 20 mL). The combined organic extracts were washed with water (3 x 20 mL), dried over anhydrous magnesium sulfate, filtered and evaporated, giving rise to ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k which were purified by crystallization from ethyl ether.

7
[ 35717-98-7 ]
[ 85418-82-2 ]
[ 1389323-26-5 ]

Yield	Reaction Conditions	Operation in experiment
35%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;	1.1. General procedures for the syntheses of ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k General procedure: The appropriate oxoquinoline derivative 5 (1.75 mmol) was stirred for 15 minutes in the presence of 750.0 mg of K2CO3 and 5.0mL of DMF, followed by the addition of diisopropyl(tosylmethoxy)phosphonate 4 (3.50 mmol). The reaction mixture was additionally stirred for 48 h at 80 °C. Afterwards, the resulting mixture was poured into water (30 mL) and extracted with methylene chloride (3 x 20 mL). The combined organic extracts were washed with water (3 x 20 mL), dried over anhydrous magnesium sulfate, filtered and evaporated, giving rise to ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k which were purified by crystallization from ethyl ether.

8
[ 35717-98-7 ]
[ 70271-77-1 ]
[ 1389323-20-9 ]

Yield	Reaction Conditions	Operation in experiment
27%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;	1.1. General procedures for the syntheses of ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k General procedure: The appropriate oxoquinoline derivative 5 (1.75 mmol) was stirred for 15 minutes in the presence of 750.0 mg of K2CO3 and 5.0mL of DMF, followed by the addition of diisopropyl(tosylmethoxy)phosphonate 4 (3.50 mmol). The reaction mixture was additionally stirred for 48 h at 80 °C. Afterwards, the resulting mixture was poured into water (30 mL) and extracted with methylene chloride (3 x 20 mL). The combined organic extracts were washed with water (3 x 20 mL), dried over anhydrous magnesium sulfate, filtered and evaporated, giving rise to ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k which were purified by crystallization from ethyl ether.

9
[ 35717-98-7 ]
[ 79607-23-1 ]
[ 1389323-22-1 ]

Yield	Reaction Conditions	Operation in experiment
35%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 48h;	General procedure: The appropriate oxoquinoline derivative 5 (1.75 mmol) was stirred for 15 minutes in the presence of 750.0 mg of K2CO3 and 5.0mL of DMF, followed by the addition of diisopropyl(tosylmethoxy)phosphonate 4 (3.50 mmol). The reaction mixture was additionally stirred for 48 h at 80 C. Afterwards, the resulting mixture was poured into water (30 mL) and extracted with methylene chloride (3 x 20 mL). The combined organic extracts were washed with water (3 x 20 mL), dried over anhydrous magnesium sulfate, filtered and evaporated, giving rise to ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k which were purified by crystallization from ethyl ether.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5055 - 5058

10
[ 35717-98-7 ]
[ 175087-43-1 ]
[ 1389323-28-7 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h;	1.1. General procedures for the syntheses of ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k General procedure: The appropriate oxoquinoline derivative 5 (1.75 mmol) was stirred for 15 minutes in the presence of 750.0 mg of K2CO3 and 5.0mL of DMF, followed by the addition of diisopropyl(tosylmethoxy)phosphonate 4 (3.50 mmol). The reaction mixture was additionally stirred for 48 h at 80 °C. Afterwards, the resulting mixture was poured into water (30 mL) and extracted with methylene chloride (3 x 20 mL). The combined organic extracts were washed with water (3 x 20 mL), dried over anhydrous magnesium sulfate, filtered and evaporated, giving rise to ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k which were purified by crystallization from ethyl ether.

11
[ 35717-98-7 ]
[ 208580-23-8 ]
[ 1389323-23-2 ]

Yield	Reaction Conditions	Operation in experiment
34%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 48h;	General procedure: The appropriate oxoquinoline derivative 5 (1.75 mmol) was stirred for 15 minutes in the presence of 750.0 mg of K2CO3 and 5.0mL of DMF, followed by the addition of diisopropyl(tosylmethoxy)phosphonate 4 (3.50 mmol). The reaction mixture was additionally stirred for 48 h at 80 C. Afterwards, the resulting mixture was poured into water (30 mL) and extracted with methylene chloride (3 x 20 mL). The combined organic extracts were washed with water (3 x 20 mL), dried over anhydrous magnesium sulfate, filtered and evaporated, giving rise to ethyl 1-[(diisopropoxyphosphoryl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylates 3a-3k which were purified by crystallization from ethyl ether.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 5055 - 5058

12
[ 35717-98-7 ]
[ 14047-28-0 ]
[ 160616-04-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With magnesium 2-methylpropan-2-olate; In water; N,N-dimethyl-formamide; at -15 - 20℃; for 44h;Inert atmosphere;	The Buchi reactor (10 L) was preheated to 150 C and traces of moisture were blown away with the nitrogen stream. The reactor was filled with argon and cooled down to RT, dry DMF (5 L, ~ 20 ppm of H2O, distilled from P2O5) was added and stirring was switched on (200 rev/min) at RT. Starting compound 1 (111.3 g, 0.576 mol) and tosylate 2b (222.1 g, 0.634 mol) were added. When the starting material was dissolved at RT, the reaction mixture was cooled down to -10 C. Then the reaction mixture was cooled to -15 C and (tBuO)2Mg (147.3, 0.864 mol) was started to be added continuously. White suspension was formed during the addition of (tBuO)2Mg at -10 C, which was continuously consumed by the reaction. The reaction was monitored by TLC. The reaction was completed in ~ 44 h. Then H2O (200 mL) was added to stop the reaction (and to destroy unreacted tosylate). The reaction mixture was slowly warmed up to RT and solvents were removed at 60 C in vacuo. The residue was dissolved in H2O (1 L) and the solution was placed into a continuous extractor and was extracted with CH2Cl2 (TLC showed none product in the water phase). The organics were dried (MgSO4) and evaporated at 30 C in vacuo. Hexane (200 mL) was added to the thick oily residue, this mixture was sonicated for 20 min, and hexane phase was removed (impurities soluble in hexane can be removed by this procedure). EtOAc (150 mL) was added to the residue and the mixture was sonicated until all product crystallized. After cooling in ice bath, the crystals were filtered off, washed (2 x 100 mL of mixture hexane/EtOAc, 5 C), and dried at 60C for 4 days (under vacuum with P2O5) to give 115.5 g (54%) of 3b (93% purity). The yield were subsequently improved to up to 91 %.
	With magnesium 2-methylpropan-2-olate; In water; N,N-dimethyl-formamide; at -15 - 20℃; for 44h;Inert atmosphere;	The Buchi reactor (10 L) was preheated to 150 C and traces of moisture were blown away with the nitrogen stream. The reactor was filled with argon and cooled down to RT, dry DMF (5 L, ~ 20 ppm of H2O, distilled from P2O5) was added and stirring was switched on (200 rev/min) at RT. Starting compound 1 (111.3 g, 0.576 mol) and tosylate 2b (222.1 g, 0.634 mol) were added. When the starting material was dissolved at RT, the reaction mixture was cooled down to -10 C. Then the reaction mixture was cooled to -15 C and (tBuO)2Mg (147.3, 0.864 mol) was started to be added continuously. White suspension was formed during the addition of (tBuO)2Mg at -10 C, which was continuously consumed by the reaction. The reaction was monitored by TLC. The reaction was completed in ~ 44 h. Then H2O (200 mL) was added to stop the reaction (and to destroy unreacted tosylate). The reaction mixture was slowly warmed up to RT and solvents were removed at 60 C in vacuo. The residue was dissolved in H2O (1 L) and the solution was placed into a continuous extractor and was extracted with CH2Cl2 (TLC showed none product in the water phase). The organics were dried (MgSO4) and evaporated at 30 C in vacuo. Hexane (200 mL) was added to the thick oily residue, this mixture was sonicated for 20 min, and hexane phase was removed (impurities soluble in hexane can be removed by this procedure). EtOAc (150 mL) was added to the residue and the mixture was sonicated until all product crystallized. After cooling in ice bath, the crystals were filtered off, washed (2 x 100 mL of mixture hexane/EtOAc, 5 C), and dried at 60C for 4 days (under vacuum with P2O5) to give 115.5 g (54%) of 3b (93% purity). The yield were subsequently improved to up to 91 %.

Reference： [1]Patent: WO2015/51874,2015,A1 .Location in patent: Page/Page column 21; 22; 6
[2]Patent: EP2860185,2015,A1 .Location in patent: Paragraph 0018; 0028

13
[ 35717-98-7 ]
[ 136834-21-4 ]
C₄₅H₄₉FN₅O₉P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		Sodium hydride (0.72 g, 18.0 mmol) was added under argon at 4 C to a stirred solution of Intermediate 2 (4 g, 6 mmol) in DMF (60 mL) (Scheme 1). The reaction mixture was stirred for additional 60 min at 4 C. Diisopropyl tosyloxymethylphosphonate (3.1 g, 9.0 mmol) was added to the reaction mixture, which was stirred under argon for additional 16 h at r.t., whereupon glacial AcOH (1.0 mL, 18.0 mmol) in DMF (10 mL) was added dropwise at 4 C to the reaction mixture. The subsequent mixture was evaporated and the crude phosphonate was purified by chromatography on silica gel (elution with gradient of 0-10% ethanol in chloroform) to yield 3.5 g (69 %): HRMS (ESI) calcd for C45H49O9N5FNaP (M+Na)+876.31441, found 876.31425.

Reference： [1]Patent: WO2019/193543,2019,A1 .Location in patent: Paragraph 0346; 0349; 0353; 0357

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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

[ CAS No. 35717-98-7 ] {[proInfo.proName]}

Quality Control of [ 35717-98-7 ]

Related Doc. of [ 35717-98-7 ]

Product Details of [ 35717-98-7 ]

Safety of [ 35717-98-7 ]

Application In Synthesis of [ 35717-98-7 ]

[ 35717-98-7 ] Synthesis Path-Downstream 1~13

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