[ CAS No. 865783-99-9 ] {[proInfo.proName]}

Name: 865783-99-9|(E)-2-Methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)phenyl dihydrogen phosphate|98%
Brand: Ambeed
SKU: A265253
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Quality Control of [ 865783-99-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 865783-99-9 ]

CAS No. :	865783-99-9	MDL No. :	MFCD22665751
Formula :	C₁₉H₂₃O₁₀PS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LXENKEWVEVKKGV-BQYQJAHWSA-N
M.W :	474.42	Pubchem ID :	11248490
Synonyms :	ON 014185	Chemical Name :	(E)-2-Methoxy-5-(((2,4,6-trimethoxystyryl)sulfonyl)methyl)phenyl dihydrogen phosphate

Safety of [ 865783-99-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
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Application In Synthesis of [ 865783-99-9 ]

* 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 [ 865783-99-9 ]

[ 865783-99-9 ] Synthesis Path-Downstream 1~13

1
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[ 865783-99-9 ]

Yield	Reaction Conditions	Operation in experiment
44.3%	Stage #1: (E)-2,4,6-trimethoxystyryl-3-O-bis(benzyl)phosphoryl-4-methoxybenzylsulfone With trimethylsilyl bromide In dichloromethane at 0℃; for 0.75h; Stage #2: With sodium thiosulfate In dichloromethane for 0.0833333h; Further stages.;
44.3%	With trimethylsilyl bromide In dichloromethane at 0℃; for 0.75h; Inert atmosphere;	1 Preparation of (E)-2,4,6-Trimethoxystyryl-3-O-phosphoryl-4-methoxybenzyl Sulfone (28); To a stirred solution of the above dibenzyl ester 27 (4.36 g, 6.7 mmol) in anhydrous dichloromethane (40 mL) under nitrogen at 0° C., was added bromotrimethylsilane (2.14 g, 14.1 mmol). The stirring was continued for 45 min at the same temperature and checked the TLC for completion of the reaction. Sodium thiosulfate (1%, 50 mL) was added to the reaction mixture and stirring was continued for an additional 5 min. The separated aqueous phase was extracted with ethyl acetate (3×25 mL). The organic extracts were concentrated in vacuo to afford the crude phosphoric acid 28, which was purified on a silica column using chloroform:methanol with increasing polarity. The purified product was concentrated in vacuo to afford pure acid 28. Yield: 44.3%; White solid mp 202-205° C. 1H NMR (DMSO-d6): δ 3.78(s, 6H, 2×OCH3), 3.85(s, 3H, OCH3), 3.86 (s, 3H, OCH3), 4.34 (s, 2H, CH2), 6.30 (s, 2H, Ar-H), 7.02 (m, 2H, Ar-H), 7.12 (d, 1H, J=15.6 Hz, CH), 7.32 (s, 2H, OH), 7.52 (s, 1H, Ar-H), 7.61 (d, 1H, J=15.6 Hz, CH). Anal. Calcd for C19H23O10PS: C, 48.10, H, 4.89. Found: C, 48.14, H, 4.92.
	With trimethylsilyl bromide In dichloromethane at 0℃; for 0.75h;	4 Example 4 (E)-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenyl dihydrogen phosphate To a stirred solution of 5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxy-phenyl dibenzyl phosphate (4.36 g, 6.7 mmol) in anhydrous DCM (40 mL) under nitrogen at 0° C. was added bromotrimethylsilane (2.14 g, 2.1 eq). The resulting mixture was stirred for 45 minutes and monitored by TLC. sodium When the reaction was complete, aqueous sodium thiosulfate (1%, 50 mL) was added and the resulting mixture was stirred for an additional 5 minutes. The organic phase was separated and the aqueous phase was extracted with ethyl acetate (3*25 mL). The combined organic extract was concentrated in vacuo to afford the crude 5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenyl dihydrogen phosphate. The product was purified column chromatography on silica eluted with a methanol/chloroform gradient to yield 1.4 g of the purified product having a melting point of 202-205° C.

Reference： [1]Reddy, M. V. Ramana; Mallireddigari, Muralidhar R.; Cosenza, Stephen C.; Pallela, Venkat R.; Iqbal, Nabisa M.; Robell, Kimberly A.; Kang, Anthony D.; Reddy, E. Premkumar [Journal of Medicinal Chemistry, 2008, vol. 51, # 1, p. 86 - 100]
[2]Current Patent Assignee: ONCONOVA THERAPEUTICS, INC. - US2010/152491, 2010, A1 Location in patent: Page/Page column 30
[3]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION; ONCONOVA THERAPEUTICS, INC. - US2008/58290, 2008, A1 Location in patent: Page/Page column 47

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Yield	Reaction Conditions	Operation in experiment
	With water In monoethylene glycol diethyl ether	5 Example 5; (E)-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenyl dihydrogen phosphate, disodium salt; To a stirred solution of 5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenyl dihydrogen phosphate (1.35 g) in ethylene glycol dimethyl ether (125 mL) was added 2N sodium hydroxide (2.4 eq). The resulting mixture was stirred for 3 h, filtered, washed with acetone (2×25 mL) and dried under vacuum to yield the 1.45 g of the disodium salt having a melting point of 152-154° C.

Reference： [1]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION; ONCONOVA THERAPEUTICS, INC. - US2008/58290, 2008, A1 Location in patent: Page/Page column 47

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[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hydroxide In 1,2-dimethoxyethane; water for 3h;	1 Preparation of (E)-2,4,6-Trimethoxystyryl-31-o-phosphate disodium-4-methoxy-benzyl Sulfone (6ab); To a stirred solution of the above phosphoric acid 28 (1.35 g, 2.85 mmol) in ethylene glycol dimethyl ether (125 mL) was added 2N sodium hydroxide (0.27 g dissolved in 13.66 mL H2O, 6.8 mmol) and stirred for 3 h. The solid formed was filtered, washed with acetone (2×25 mL) and dried under vacuum to get the product 6ab. Yield: 98%; white solid mp 152-154° C. 1H NMR (D2O): δ 3.68 (s, 6H, 2×OCH3), 3.71 (s, 3H. OCH3), 3.78 (s, 3H. OCH3), 4.35 (s, 2H, CH2), 5.92 (s, 2H, Ar-H), 6.91 (s, 2H, Ar-H), 6.97 (d, 1H, J=15.6 Hz, CH), 7.39 (s, 1H, Ar-H), 7.43 (d, 1H, J=15.6 Hz, CH). 13C NMR (D2O): δ 164.4, 161.7, 151.1, 143.8, 136.8, 125.9, 123.4, 120.6, 120.2, 113.1, 103.4, 91.1, 61.0, 56.4, 56.2, 55.9. Anal. (C19H21O10Na2PS): C, H.

Reference： [1]Current Patent Assignee: ONCONOVA THERAPEUTICS, INC. - US2010/152491, 2010, A1 Location in patent: Page/Page column 30

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Yield	Reaction Conditions	Operation in experiment
	With water In tetrahydrofuran Cooling with ice;	3 EXAMPLE 3Phosphorylation of Compound 013100 Using POCl3 The following Example is directed to the preparation of Compound 013105 by phosphorylation of Compound 013100 using POCl3.Scheme 7 below depicts the method for the synthesis of (E)-2,4,6-(trimethoxystyryl)-3-O-phosphate disodium-4-methoxybenzyl sulfone (Compound 013105).50 grams of compound 20 is dissolved in 500 ml of THF. To the solution 125 ml of Triethylamine is added. The solution is filtered to get the clear solution. This is taken into a pressure equalizing dropping funnel.Into a 2 lit three necked flask 50 ml of Phosphorous oxychloride in 150 ml of THF is taken. The reactor is fitted with a mechanical stirrer and a reflux condenser and kept in an ice bath to attain 0 C degree. To this cooled solution, the solution in the pressure equalizing funnel (Compound 013100+Et3N+THF) is added drop-wise for a period of 90 minutes (TLC shows the completion of reaction).The ice bath is allowed to attain room temperature and the stirring is continued for 2½ hrs. At this stage the reaction mixture develops light yellow color with the formation of water soluble precipitate.The reaction mixture is again taken into the pressure equalizing dropping funnel. Into the 2 lit flask 500 ml of ice cubes are taken. The flask is cooled in an ice bath. The reaction mixture is added to the ice cubes over a period of 45 minutes. After completion of the addition, stirring is continued for 5 to 7 hrs. To the contents of the flask 200 ml of 50% potassium hydroxide solution (85%) is added slowly. During the addition the flask is maintained in an ice bath. After the addition of KOH solution stirring is continued for a period of 40 minutes.The reaction mixture is allowed to settle for the separation of organic layer. The organic layer is separated and tested for the presence of Compound 013100 and the other impurity that appeared above the Compound 013100 in TLCThe aqueous layer is washed twice with THF (2×400 ml portions) and each time the organic layer is tested for the impurities and discarded. At this stage the aqueous layer is totally free from the impurities. Finally the aqueous layer is washed with 500 ml of ethyl acetate.The aqueous layer is taken in a two litre RB which is maintained in an ice bath. To this dilute HCl solution (1:1, 135 ml) is added drop-wise under moderate stirring. During the addition the phosphoric acid of Compound 20 starts separation as light yellow gummy solid. Stirring is continued for 3½ hrs to get light yellow granulated solid. The solid compound is filtered dried and weighed (50 grams)The solid compound is dissolved in 400 ml of methanol and the solution is filtered to remove the insoluble and suspended impurities. The clear solution is taken in a conical flask equipped with a magnetic stirrer. The assembly is kept in a water bath. To the solution, 32 ml of 25% sodium hydroxide solution is added drop-wise under stirring. During the addition a white phosphate salt formation is observed. After completion of the addition of NaOH solution, the PH of the solution is found to be 8. Stirring is continued for 6 hrs for the completion of phosphate salt formation.The phosphate salt is filtered and the conical flask is washed with 100 ml of acetone to transfer on to the filter funnel. The precipitate is washed with 2×100 ml portions of acetone. Finally the salt is dried under vacuum. The dried salt weighed 50 grams. The Compound 013105 is found to be matching with the standard sample.

Reference： [1]Current Patent Assignee: ONCONOVA THERAPEUTICS, INC. - US2010/152491, 2010, A1 Location in patent: Page/Page column 40-41

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[ 762-04-9 ]
[ 865784-11-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ON-013105 With carbon tetrabromide; triethylamine In acetonitrile at 0 - 20℃; for 0.166667h; Stage #2: phosphonic acid diethyl ester In acetonitrile at 0℃; for 2h;	6 Example 6; (E)-5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenyl diethyl phosphate; To a stirred solution of 5-((2,4,6-trimethoxystyrylsulfonyl)methyl)-2-methoxyphenyl dihydrogen phosphate (1.9 g, 4.8 mmol) in acetonitrile (24 mL) at room temperature, was added carbon tetrabromide (1.94 g, 1.22 eq) and triethylamine (0.728 g, 1.5 eq). The resulting mixture was stirred for 10 minutes and than cooled to 0° C. in an ice-water bath. Diethyl phosphite (1.51 g, 1.2 eq) dissolved in acetonitrile (16 mL) was added dropwise to the cooled reaction mixture. The reaction mixture was stirred for 2 h and monitored by TLC. The reaction was terminated by dropwise addition of aqueous potassium dihydrogen phosphate (10 mL, 0.5 M). The resulting mixture was extracted with ethyl acetate (3×30 mL). The combined organic extract was dried (Na2SO4) and concentrated in vacuo to yield the desired product.

Reference： [1]Current Patent Assignee: COMMONWEALTH SYSTEM OF HIGHER EDUCATION; ONCONOVA THERAPEUTICS, INC. - US2008/58290, 2008, A1 Location in patent: Page/Page column 47

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