1623-07-0|Benzyl dihydrogen phosphate| Ambeed

CAS No. :	1623-07-0
Formula :	C₇H₉O₄P
M.W :	188.12
SMILES Code :	O=P(O)(OCC1=CC=CC=C1)O
MDL No. :	MFCD02177841
InChI Key :	YTFJQDNGSQJFNA-UHFFFAOYSA-N
Pubchem ID :	2784427

Safety of [ 1623-07-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 1623-07-0 ]

* 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 [ 1623-07-0 ]

[ 1623-07-0 ] Synthesis Path-Downstream 1~48

1
[ 110-86-1 ]
[ 1623-07-0 ]
[ 120209-62-3 ]
[ 109653-33-0 ]

References: [1]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 935,937.

2
[ 1623-08-1 ]
[ 1623-07-0 ]

References: [1]Journal of the Chemical Society,1956,p. 1371,1375.

3
[ 64108-81-2 ]
[ 1623-07-0 ]

References: [1]Journal of the American Chemical Society,1957,vol. 79,p. 3741,3745.

4
[ 1623-07-0 ]
[ 63-37-6 ]
[ 63-38-7 ]

References: [1]Journal of the Chemical Society,1958,p. 546,549, 550.

5
[ 100-44-7 ]
[ 1623-07-0 ]

References: [1]Journal of Biochemistry,1930,vol. 11,p. 164,168.
Chemisches Zentralblatt,1930,vol. 101,p. 2906.

6
[ 1623-07-0 ]
[ 538-75-0 ]
[ 51478-53-6 ]

References: [1]Journal of the American Chemical Society,1958,vol. 80,p. 6204,6206, 6212.
[2]Journal of the American Chemical Society,1958,vol. 80,p. 6204,6206, 6212.

7
[ 100-51-6 ]
[ 1623-07-0 ]

Yield	Reaction Conditions	Operation in experiment
79.4%	With phosphoric acid; triethylamine; trichloroacetonitrile; at 0 - 20℃; for 3h;	General procedure: To a dry round bottom flask was added alcohol (6.0 equiv.), crystalline phosphoric acid (1.0 equiv.) and triethylamine (4.5 equiv.), and then was added trichloroacetonitrile (5.0 equiv.) dropwise at 0 C after the acid was dissolved by stirring. The reaction was then stirred at room temperature for 3 h, followed by addition of water to the reaction mixture. The solution was then extracted three times with ethyl ether, and the water layer was cooled in an ice bath and cyclohexylamine (10.0 equiv.) was added. The product was precipitated by adding acetone.
59%		General procedure: To a solution of the alcohol (1 mmol) in acetonitrile (1 mL), trichloroacetonitrile (2.4 mmol) is added, followed by dropwise addition of tetrabutylammonium dihydrogenphosphate (2.0 mmol) in acetonitrile (5 mL). The reaction mixture is stirred at room temperature for two hours, or until all the starting material is consumed. The solvent is removed in vacuo and the crude material is pre-purified by flash chromatography on silica gel (isopropanol/conc. aq NH4OH/H2O 7:2:1). The column fractions which show the presence of phosphate on TLC (e.g., with molybdate reagent) are combined and concentrated under reduced pressure. A Dowex 50WX8 ion-exchange column of 8 cm tall and 1 cm diameter is loaded and equilibrated with a mixture of conc. NH4OH/H2O 3:1 and afterward flushed with a buffer solution of 0.025 M NH4HCO3 until the pH reaches 8.0. The silica column residue is percolated through the DOWEX column with the same NH4OH buffer, collected, and dried either by lyophilization or by evaporation under reduced pressure until excess ammonium hydrogen carbonate is evaporated. The residual ammonium organophosphates are isolated as white solids

References: [1]Tetrahedron Letters,2021,vol. 68.
[2]Tetrahedron Letters,2013,vol. 54,p. 1690 - 1692.
[3]Journal of the American Chemical Society,2014,vol. 136,p. 108 - 111.
[4]Helvetica Chimica Acta,1946,vol. 29,p. 2006,2012.
[5]Chemical and Pharmaceutical Bulletin,1973,vol. 21,p. 2438 - 2443.
[6]Angewandte Chemie,1960,vol. 72,p. 236 - 249.
[7]Chemische Berichte,1961,vol. 94,p. 328 - 337.
[8]Chemische Berichte,1961,vol. 94,p. 996 - 1007.
[9]Journal of Organic Chemistry,1978,vol. 43,p. 992 - 996.
[10]Advanced Synthesis and Catalysis,2005,vol. 347,p. 1155 - 1162.
[11]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 152 - 155.

8
[ 1623-07-0 ]
[ 57775-14-1 ]
[ 50580-24-0 ]

References: [1]Chemische Berichte,1965,vol. 98,p. 1038 - 1044.

9
[ 1623-07-0 ]
Phosphoric acid naphthalen-2-yl ester pyridin-2-yl ester; compound with cyclohexylamine [ No CAS ]
[ 47505-02-2 ]

References: [1]Chemische Berichte,1965,vol. 98,p. 1038 - 1044.

10
[ 1623-07-0 ]
[ 109087-23-2 ]
(S)-4-[(S)-2-[(3aR,4S,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2-(benzyloxy-hydroxy-phosphoryloxy)-ethylsulfanyl]-2-tert-butoxycarbonylamino-butyric acid methyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 1599 - 1603.

11
[ 37173-17-4 ]
[ 1623-07-0 ]

References: [1]Synthesis,1988,p. 142 - 144.

12
[ 51478-53-6 ]
[ 1623-07-0 ]

References: [1]Bulletin of the Chemical Society of Japan,1981,vol. 54,p. 1891 - 1892.

13
[ 107-46-0 ]
[ 100-51-6 ]
[ 1623-07-0 ]

References: [1]Bulletin of the Chemical Society of Japan,1985,vol. 58,p. 3393 - 3394.

14
[ 67-56-1 ]
[ 1623-07-0 ]
[ 97194-51-9 ]

References: [1]Chemische Berichte,1962,vol. 95,p. 1657 - 1663.

15
[ 71-23-8 ]
[ 1623-07-0 ]
[ 97617-70-4 ]

References: [1]Chemische Berichte,1962,vol. 95,p. 1657 - 1663.

16
[ 64-17-5 ]
[ 1623-07-0 ]
[ 29690-06-0 ]

References: [1]Chemische Berichte,1962,vol. 95,p. 1657 - 1663.

17
[ 1623-07-0 ]
[ 67-63-0 ]
[ 97617-72-6 ]

References: [1]Chemische Berichte,1962,vol. 95,p. 1657 - 1663.

18
[ 1623-07-0 ]
N,N',N''-tricyclohexyl-guanidine salt of O^5'-<cyclohexylamino-hydroxy-phosphoryl>-guanosine [ No CAS ]
[ 109653-33-0 ]

References: [1]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 935,937.

23
[ 100-51-6 ]
metaphosphoric acid ethyl ester [ No CAS ]
[ 1623-07-0 ]

References: [1]Chemische Berichte,1911,vol. 44,p. 2085.

24
phosphoric acid [ No CAS ]
[ 946-80-5 ]
[ 1623-07-0 ]
[ 108-95-2 ]

References: [1]Journal of the Chemical Society,1954,p. 3854.

25
[ 96652-94-7 ]
[ 1623-07-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 1129 - 1136.

26
[ 1623-07-0 ]
[ 99478-15-6 ]
[ 959586-68-6 ]

Yield	Reaction Conditions	Operation in experiment
	With silver carbonate; In toluene; at 95℃; for 16h;	Step B: Benzyl di(octyloxycarbonyloxy-1-ethyl)phosphate (36); Chloroethyl octyloxyformate (35) (3.73 g) was added to a suspension of <strong>[1623-07-0]benzyl phosphate</strong> (1.45 g) and silver carbonate (6 g) in toluene and the mixture stirred at 95 C. for 16 hours. The suspension was filtered to remove the solid. After concentration under reduced pressure, the filtrate was purified using chromatography (silica gel, 20% ethyl acetate in hexane) to provide 1.75 g of the title compound (36) as a colorless oil.

References: [1]Patent: US2007/281909,2007,A1 .Location in patent: Page/Page column 55.

27
[ 100-51-6 ]
NaCpW(CO)3 [ No CAS ]
[ 1623-07-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 1129 - 1136.

28
phosphorous acid diallyl ester benzyl ester [ No CAS ]
[ 1623-07-0 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 1129 - 1136.

29
[ 1623-07-0 ]
[ 530-62-1 ]
benzyl phosphoroimidazolidate [ No CAS ]

References: [1]Carbohydrate Research,2008,vol. 343,p. 167 - 178.

30
3-phenylpropylcarbamoyloxymethyl chloride [ No CAS ]
[ 1623-07-0 ]
[ 959586-55-1 ]

Yield	Reaction Conditions	Operation in experiment
82%		Step B: Benzyl Diphenylpropylcarbonyloxymethyl Phosphate (28); A solution of 1.8 g of benzylphosphoric acid in 90 mL of MeOH and 30 mL of water was treated with Dowex 50WX2-400 (153 mL) at room temperature for 2 hours. The resin was removed by filtration using a glass filter and 2.5 g of silver carbonate powder was added to the filtrate. After the resulting suspension was heated at 80 C. for 1 hour, all solvent was removed under reduced pressure to dryness. 300 mL of dry toluene was added to the silver salt followed by the addition of phenylpropylcarbamoyloxymethyl chloride and the suspension was heated at 100 C. overnight. After the solid was removed by filtration, the product was purified by silica gel chromatography using hexane/ethylacetate (3:1) as the eluent to provide benzyl diphenylpropylcarbonyloxymethyl phosphate (28) as a colorless liquid (2 g, 82%). 1H NMR (CDCl3, 400 MHz): δ 7.10-7.38 (m, 15H), 5.56-5.64 (m, 4H), 5.08 (d, 2H, J=8.0 Hz), 2.61 (t, 4H, J=8.0 Hz), 2.32(t, 4H, J=8.0 Hz), 1.92 (q, 4H, J=8.0 Hz).

References: [1]Patent: US2007/281909,2007,A1 .Location in patent: Page/Page column 54.

31
[ 1623-07-0 ]
[ 1522124-96-4 ]