69260-71-5|1-((2R,3S,4S,5R)-3,4-Dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione| Ambeed

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Quality Control of [ 69260-71-5 ] Purity: 98% SDS Specification

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Product Details of [ 69260-71-5 ]

CAS No. :	69260-71-5
Formula :	C₉H₁₁FN₂O₅
M.W :	246.19
SMILES Code :	O=C1NC(C(F)=CN1[C@@H]2O[C@H](C)[C@@H](O)[C@@H]2O)=O

Safety of [ 69260-71-5 ]

Application In Synthesis of [ 69260-71-5 ]

* 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 [ 69260-71-5 ]

[ 69260-71-5 ] Synthesis Path-Downstream 1~35

1
[ 40635-66-3 ]
[ 69260-71-5 ]
[ 71609-10-4 ]

References: [1]Journal of Medicinal Chemistry,1979,vol. 22,p. 1330 - 1335.

2
[ 124012-42-6 ]
[ 3086-62-2 ]
[ 66335-38-4 ]
[ 118-41-2 ]
[ 69260-71-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 2568 - 2571.

3
[ 77180-87-1 ]
[ 69260-71-5 ]

References: [1]Collection of Czechoslovak Chemical Communications,1980,vol. 45,p. 3217 - 3230.

4
[ 76462-82-3 ]
[ 69260-71-5 ]

Yield	Reaction Conditions	Operation in experiment
182 g	With ammonia; In methanol; at 10 - 15℃; for 5.0h;	In the reaction flask, 280 g of compound (IV), 750 ml of 1% ammonia methanol were charged, and the temperature was controlled at 10-15 C.The reaction was kept for 5 hours, and after the reaction was finished, the methanol was concentrated and recovered.Adding fresh methanol directly to the crude solid product, stirring and crystallizing, crystallizing at 0 degree for 5 hours, filtering,Drying to give a white crystalline solid (I) 182 g,

References: [1]Helvetica Chimica Acta,1982,vol. 65,p. 1522 - 1537.
[2]Organic Letters,2012,vol. 14,p. 3348 - 3351.
[3]Patent: CN108117574,2018,A .Location in patent: Paragraph 0016; 0017; 0018; 0019; 0020.

5
[ 78948-09-1 ]
[ 15958-99-3 ]
[ 118967-81-0 ]
[ 118967-80-9 ]
[ 118967-80-9 ]
[ 69260-71-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 2547 - 2554.

6
[ 15958-99-3 ]
[ 118967-81-0 ]
[ 118967-80-9 ]
[ 118967-80-9 ]
[ 69260-71-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 2547 - 2554.

7
[ 15958-99-3 ]
[ 118967-81-0 ]
[ 118967-80-9 ]
[ 118967-80-9 ]
[ 69260-71-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 2547 - 2554.
[2]Journal of the Chemical Society. Perkin transactions I,1988,p. 2547 - 2554.

8
[ 78948-09-1 ]
[ 69260-71-5 ]
[ 118967-92-3 ]
[ 119003-15-5 ]
[ 118967-84-3 ]
[ 118967-88-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 2547 - 2554.

9
[ 69260-71-5 ]
[ 51-21-8 ]

References: [1]Journal of Medicinal Chemistry,1988,vol. 31,p. 1094 - 1098.
[2]Biological and Pharmaceutical Bulletin,1995,vol. 18,p. 172 - 175.
[3]Biological and Pharmaceutical Bulletin,1997,vol. 20,p. 935 - 938.

10
[ 69260-71-5 ]
[ 118967-92-3 ]
[ 119003-15-5 ]
[ 118967-84-3 ]
[ 118967-88-7 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 2547 - 2554.

11
[ 61960-57-4 ]
[ 69260-71-5 ]
3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoic acid (2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-methyl-tetrahydro-furan-3-yl ester [ No CAS ]
3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoic acid (2R,3R,4R,5R)-2-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-5-methyl-tetrahydro-furan-3-yl ester [ No CAS ]

References: [1]Pharmazie,1997,vol. 52,p. 480 - 481.

Yield	Reaction Conditions	Operation in experiment
		B. 5'-deoxy-5-fluorouridine To a solution of 35.1 g (0.07% m) of 5'-deoxy-5'-iodo-5-fluorouridine and 2.93 g of alpha,alpha'-azoisobutyronitrile in 1100 ml of methanol, a solution of 37.4 g of tributyltin hydride in 310 ml of toluene is added. The mixture is heated at reflux for 2 hours and the clear solution thus obtained is concentrated under vacuum until a semisolid residue, which is dispersed in 900 ml of petroleum ether. The solid is filtered and treated with 1200 ml of water; the tin salts are separated by filtration and the filtrate is concentrated under vacuum; the residue is crystallized with. 500 ml of hot ethanol to obtain 12.3 g di 5'-deoxy-5-fluorouridine. M.p.=188÷189 C., purity (HPLC)=99.91% and [alpha]D=+18.4 (c=0.42, H2O).
		For the effective combination of the 5'-deoxycytidine derivative represented by the formula (I) with 5-FU or its derivative for the treatment of cancer with an improved efficacy and safety profile, a 5-FU derivative can be selected from the group consisting of: 5-fluoro-1-(2-tetrahydrofuryl)uracil, 1-(n-hexyloxycarbonyl)-5-fluorouracil, 5'-deoxy-5-fluorouridine, 5'-deoxy-5-fluoro-N4 -(n-propoxycarbonyl)cytidine, N4 -(n-butoxycarbonyl)-5'-deoxy-5-fluorocytidine, ...
		For the combination of a 5'-deoxy-cytidine derivative represented by the formula (I) with 5-FU or a derivative thereof for the treatment of cancer with an improved efficacy and safety profile, the 5-FU derivative is preferably selected from the group consisting of: 5-fluoro-1-(2-tetrahydrofuryl)uracil, 1-(n-hexyloxycarbonyl)-5-fluorouracil, 5'-deoxy-5-fluorouridine, 5'-deoxy-5-fluoro-N4 -(n-propoxycarbonyl)cytidine, N4 -(n-butoxycarbonyl)-5'-deoxy-5-fluorocytidine, 5'-deoxy-5-fluoro-N4 -(n-pentyloxycarbonyl)cytidine, 5'-deoxy-5-fluoro-N4 -(isopentyloxycarbonyl)cytidine, 5'-deoxy-5-fluoro-N4 -(n-hexyloxycarbonyl)cytidine, 5'-deoxy-N4 -[(2-ethylbutyl)oxycarbonyl]-5-fluorocytidine, ...

		30 ml of a solution of 2,4-bis (trimethylsilyl)-5-fluorouracil (prepared from 5.2 g of fluorouracil and 20 ml of hexamethyldisilazane) in methylene chloride were added to a solution of 8.1 g of freshly distilled methyl (5-deoxy-2,3-di-O-acetyl)-D-ribofuranoside in 81 ml of methylene chloride. The mixture was cooled in ice and treated while stirring with a solution of 7 ml of trimethylsilyl-trifluoro-methanesulphonate in 8 ml of methylene chloride. The mixture was left to stand at room temperature for 20 hours, poured into 200 ml of saturated aqueous sodium hydrogen carbonate solution, the mixture was stirred for 30 minutes and then extracted 3 times with 100 ml of methylene chloride each time. The combined extracts were washed twice with 50 ml of water each time, dried over anhydrous sodium sulphate, concentrated to 60 ml under reduced pressure without heating and, after the addition of 60 ml of hexane, concentrated under the same conditions. The residue was left to stand for 4 hours in a refrigerator, the crystals were filtered off, washed with a cold 1:1 mixture of ethyl acetate and hexane and finally with ethyl acetate. There were obtained 7 g of pure 1-(5-deoxy-2,3-di-O-acetyl-beta-D-ribofuranosyl)-5-fluorouracil, m.p. 179-181 C.; [beta]D20 =+34.6 (c=1.0 in methanol). 2.5 g of 1-(5-deoxy-2,3-di-O-acetyl-beta-D-ribofuranosyl)-5-fluorouracil were heated under reflux in 60 ml of methanol in the presence of 0.3 ml of triethylamine until starting material could no longer be detected by thin-layer chromatography. The colourless, clear solution was concentrated under reduced pressure and the white, crystalline material obtained was recrystallized from water. There was obtained pure 5'-deoxy-5-fluorouridine, m.p. 192-193 C., in 98% yield.
		Pyrimidine analogs such as Ancitabine, Azacitidine, 6-Azauridine, Carmofur, Cytarabine, Doxifluridine, Enocitabine, Floxuridine, Fluroouracil and Tegafur;

13
[ 18162-48-6 ]
[ 205533-35-3 ]
[ 69260-71-5 ]
[ 500882-63-3 ]

References: [1]European Journal of Organic Chemistry,2002,p. 3622 - 3631.

14
[ 18162-48-6 ]
[ 69260-71-5 ]
3'-O-(tert-butyldimethylsilyl)-5'deoxy-5-fluorouridine [ No CAS ]
2'-O-(tert-butyldimethylsilyl)-5'deoxy-5-fluorouridine [ No CAS ]

References: [1]European Journal of Organic Chemistry,2002,p. 3622 - 3631.

15
[ 69260-71-5 ]
3'-(5'-deoxy-5-fluoro)uridylic acid mono[(2R)-2,3-dihydroxypropyl] ester [ No CAS ]

References: [1]European Journal of Organic Chemistry,2002,p. 3622 - 3631.

16
[ 69260-71-5 ]
Hexadecanoic acid (R)-3-[(2R,3S,4R,5R)-5-(5-fluoro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-methyl-tetrahydro-furan-3-yloxy]-hydroxy-phosphoryloxy}-2-hydroxy-propyl ester [ No CAS ]

References: [1]European Journal of Organic Chemistry,2002,p. 3622 - 3631.

17
[ 37105-93-4 ]
[ 69260-71-5 ]