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Chemical Structure| 65-46-3
Chemical Structure| 65-46-3
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Product Details of [ 65-46-3 ]

CAS No. :65-46-3 MDL No. :MFCD00006545
Formula : C9H13N3O5 Boiling Point : -
Linear Structure Formula :- InChI Key :UHDGCWIWMRVCDJ-XVFCMESISA-N
M.W : 243.22 Pubchem ID :6175
Synonyms :
Cytosine β-D-riboside;Cytosine-1-β-D-ribofuranoside;NSC 20258;β-D-Cytidine

Safety of [ 65-46-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 65-46-3 ]

* 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.

  • Upstream synthesis route of [ 65-46-3 ]
  • Downstream synthetic route of [ 65-46-3 ]

[ 65-46-3 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 65-46-3 ]
  • [ 3066-86-2 ]
YieldReaction ConditionsOperation in experiment
72% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at 25℃; for 0.5 h; Typical procedure for the bromination of unprotected nucleosides: DBH (323 mg, 1.13 mmol) was added to a stirred solution of 1d (500 mg, 2.05 mmol) in DMF (5 mL). The resulting pale-yellow solution was stirred at room temperature for 20 minutes or until TLC showed absence of starting material and formation of less polar product. Volatiles were evaporated and the residue was coevaporated with MeCN. The resulting pale solid was crystallized from hot acetone to give 2d (500 mg, 75percent) as colorless crystals with data as reported.14
69% With sodium azide; bromoisocyanuric acid monosodium salt In water; acetonitrile at 20℃; for 3 h; General procedure: 2'-O-Methyluridine (5, 0.103 g, 0.4 mmol) was dissolved in aqueous acetonitrile solution(H2O:CH3CN 1:9, 5 mL) under stirring. NaN3 (0.104 g, 1.6 mmol) was added, followed by addition of SMBI (0.101 g, 0.44 mmol) at r.t. and the mixture was stirred. Progress of the reaction was followedby TLC. On completion of the reaction after 1.5 h, the reaction mixture was filtered, evaporated todryness under reduced pressure and coevaporated with acetonitrile (2 × 2 mL). The crude reactionmixture was purified by column chromatography (4percent–6percent MeOH in DCM, v/v) to afford bromonucleoside 6 (0.117 g, 93percent) in pure form as a white solid
Reference: [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5634 - 5644
[2] Synthesis, 2009, # 23, p. 3957 - 3962
[3] Tetrahedron Letters, 2012, vol. 53, # 26, p. 3333 - 3336
[4] Molecules, 2013, vol. 18, # 10, p. 12740 - 12750
[5] Journal of the American Chemical Society, 1995, vol. 117, # 2, p. 704 - 714
[6] Journal of Organic Chemistry, 1982, vol. 47, # 6, p. 1018 - 1023
[7] Journal of the American Chemical Society, 1955, vol. 77, p. 2393
  • 2
  • [ 65-46-3 ]
  • [ 316-46-1 ]
Reference: [1] Patent: US4122251, 1978, A,
  • 3
  • [ 65-46-3 ]
  • [ 1024-99-3 ]
Reference: [1] Organic Preparations and Procedures International, 2018, vol. 50, # 3, p. 332 - 342
  • 4
  • [ 107-71-1 ]
  • [ 65-46-3 ]
  • [ 10578-79-7 ]
  • [ 2140-64-9 ]
  • [ 2140-61-6 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 12, p. 2373 - 2377
  • 5
  • [ 13233-20-0 ]
  • [ 156-81-0 ]
  • [ 50574-59-9 ]
  • [ 65-46-3 ]
Reference: [1] Nature Chemistry, 2017, vol. 9, # 4, p. 303 - 309
  • 6
  • [ 107-20-0 ]
  • [ 65-46-3 ]
  • [ 55662-66-3 ]
Reference: [1] Chemical Research in Toxicology, 2001, vol. 14, # 12, p. 1612 - 1619
  • 7
  • [ 17287-03-5 ]
  • [ 65-46-3 ]
  • [ 20594-00-7 ]
  • [ 2140-72-9 ]
  • [ 2140-64-9 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 19, p. 3865 - 3868
[2] Journal of Organic Chemistry, 1980, vol. 45, # 19, p. 3865 - 3868
[3] Journal of Organic Chemistry, 1980, vol. 45, # 19, p. 3865 - 3868
[4] Journal of the Chemical Society, Perkin Transactions 1, 1980, p. 2787 - 2792
[5] Journal of the Chemical Society, Perkin Transactions 1, 1980, p. 2787 - 2792
  • 8
  • [ 65-46-3 ]
  • [ 74-88-4 ]
  • [ 2140-72-9 ]
Reference: [1] Patent: US5646265, 1997, A,
  • 9
  • [ 684-93-5 ]
  • [ 65-46-3 ]
  • [ 2140-72-9 ]
  • [ 2140-64-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 20, p. 5943 - 5946[2] Angew. Chem., 2018, vol. 130, # 20, p. 6050 - 6054,5
  • 10
  • [ 17287-03-5 ]
  • [ 65-46-3 ]
  • [ 20594-00-7 ]
  • [ 2140-72-9 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, p. 2947 - 2949
[2] Bulletin of the Chemical Society of Japan, 1986, vol. 59, p. 2947 - 2949
  • 11
  • [ 1899-02-1 ]
  • [ 65-46-3 ]
  • [ 2140-69-4 ]
  • [ 20594-00-7 ]
  • [ 2140-72-9 ]
Reference: [1] Synthetic Communications, 1980, vol. 10, # 1, p. 25 - 36
[2] Synthetic Communications, 1980, vol. 10, # 1, p. 25 - 36
  • 12
  • [ 65-46-3 ]
  • [ 74-88-4 ]
  • [ 20594-00-7 ]
  • [ 2140-72-9 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 20, p. 5846 - 5859
[2] Journal of Organic Chemistry, 1991, vol. 56, # 20, p. 5846 - 5859
  • 13
  • [ 186581-53-3 ]
  • [ 65-46-3 ]
  • [ 20594-00-7 ]
  • [ 2140-72-9 ]
Reference: [1] Helvetica Chimica Acta, 1996, vol. 79, # 8, p. 2114 - 2136
[2] Carbohydrate Research, 1981, vol. 91, p. 31 - 38
[3] Carbohydrate Research, 1981, vol. 91, p. 31 - 38
  • 14
  • [ 65-46-3 ]
  • [ 1147-23-5 ]
YieldReaction ConditionsOperation in experiment
85.1% With iodine; iodic acid; acetic acid In tetrachloromethane; water at 20 - 40℃; Synthesis of 5-iodocytidine 191: A mixture of cytidine 190 (15.0 g, 61.7 mmol) in 225 mL of acetic acid and 225 mL of carbon tetrachioride was warmed to 40 CC, and iodine (9.6 g, 75.7 mmol) was added.To the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of water within 10 mm. The reaction mixture was stirred at 40 CC for 6 h and stirred at room temperature overnight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column using dichloromethane—methanol(15:1 to 10:1 to5:1) asgradienteluents resulting in 19.4g (85.1percent) desiredproduct 5-iodocytidine (191).
85.1% With iodine; iodic acid In tetrachloromethane; water; acetic acid at 40℃; for 6 h; Synthesis of 5-iodocytidine 1 91 : A mixture of cytidine 190 (15.0 g, 61 .7 mmol) in 225 mL of acetic d and 225 mL of carbon tetrachloride was warmed to 40 °C, and iodine (9.6 g, 75.7 mmol) was added. the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of ter within 10 min. The reaction mixture was stirred at 40 °C for 6 h and stirred at room temperature ernight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated der reduced pressure. The residue was purified by flash chromatography on a silica gel column using hloromethane-methanol (15:1 to 1 0:1 to 5:1 ) as gradient eluents resulting in 1 9.4 g (85.1 percent) desired duct 5-iodocytidine (191 ).
85.1% With iodine; iodic acid; acetic acid In tetrachloromethane; water at 20 - 40℃; Synthesis of 5-iodocytidine 191: A mixture of cytidine 190 (15.0 g, 61.7 mmol) in 225 mL of acetic acid and 225 mL of carbon tetrachloride was warmed to 40 °C, and iodine (9.6 g, 75.7 mmol) was added. To the stirred reaction mixture was added slowly a solution of iodic acid (9.6 g, 54.6 mmol) in 25 mL of water within 10 min. The reaction mixture was stirred at 40 °C for 6 h and stirred at room temperature overnight. Upon completion of the reaction as monitored by TLC, the reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column using dichloromethane-methanol (15:1 to 10:1 to 5:1) as gradient eluents resulting in 19.4 g (85.1 percent) desired product 5-iodocytidine (191).
72.4% With N-iodo-succinimide In methanol at 40 - 70℃; The cytidine (0.66 g, 2.7 mol) was added to the three-necked flask,N-iodosuccinimide (0.60 g, 2.4 mol) and 50 ml of methanol, and the temperature was raised to 40-70 ° C. The reaction was stirred for 6-12 hours.Cooled to room temperature, filtered, added with silica gel and removed by rotary evaporation. The column chromatography gave 0.48 g of a pale yellow solid in 72.4percent yield.
51% With iodine; iodic acid; acetic acid In tetrachloromethane; water at 40℃; for 2 h; General procedure: The suspension of nucleosides 2a,b (19 mmol) in water (5.7 mL) was treated with HIO3(9.7 mmol, 1.7 g), AcOH (15.2 mL) and a solution of iodine (11.22 mmol, 2.85 g) inCCl4 (3.8 mL). The resulting mixture was stirred at 40C for 2 h until the starting materialwas consumed or some by-product was formed (monitored by HPLC). After that,water (20 mL) was added. The reaction mixture was cooled to 4C and filtered. The precipitatewas washed with water (2 £ 10 mL). The combined solutions were diluted withwater (250 ml) and extracted with benzene (3 £ 150 mL). The aqueous layer was evaporatedunder reduced pressure. The product was purified by RPC in a linear gradient ofEtOH in water (0–30percent) to give the product 3a,b.

Reference: [1] Patent: WO2015/196130, 2015, A2, . Location in patent: Page/Page column 634; 635
[2] Patent: WO2015/196128, 2015, A2, . Location in patent: Page/Page column 642
[3] Patent: EP2918275, 2015, A1, . Location in patent: Paragraph 2219; 2220
[4] Patent: EP2918275, 2016, B1, . Location in patent: Paragraph 2219; 2220
[5] Journal of the American Chemical Society, 2015, vol. 137, # 1, p. 34 - 37
[6] Synthesis, 2003, # 7, p. 1039 - 1042
[7] Patent: CN106674316, 2017, A, . Location in patent: Paragraph 0015-0016; 0019-0020
[8] Synthesis, 2009, # 23, p. 3957 - 3962
[9] Tetrahedron Letters, 1999, vol. 40, # 51, p. 8961 - 8964
[10] Organic Preparations and Procedures International, 2018, vol. 50, # 3, p. 332 - 342
[11] Chemical & Pharmaceutical Bulletin, 1982, vol. 30, # 8, p. 2688 - 2697
  • 15
  • [ 108-24-7 ]
  • [ 65-46-3 ]
  • [ 3768-18-1 ]
YieldReaction ConditionsOperation in experiment
96% for 3 h; Reflux In a 500 mL three-necked flask was added 50.0 g of Compound 3 powder and 250 mL of acetonitrile and 25 mL of acetic anhydride, stirred and refluxed for 3 h, cooled to room temperature and filtered with suction. The solid was washed with acetonitrile twice and the filter cake was dried to give 56.3 g of compound 4 with a yield of 96.0 percent.
95% for 0.0111111 h; Microwave radiation To a solution of cytidine (1.22 g, 5.00 mmol) in DMF(40 mL) is added acetic anhydride (0.94 mL, 10.00 mmol). The solution is treated with microwave radiation (Panasonic, 1000 Watts) at full power for 40 seconds. The solution is concentrated in vacuo and the residue is co-evaporated with methanol (2.x.20 mL) to give 4-N-acetyl-cytidine (1.43 g, 95.0percent) as a white powder. MS (FAB):m/z 286 (MH+).
87% for 24 h; Cytidine (100.Og, 0.41 mol) was dissolved in DMF (500 ml), acetic anhydride (42.5 ml, 45.9 g, 0.45 mol) was added and the whole was left for 24 h. Solvent was evaporated, the residue boiled with methanol (40 ml) and cooled. Crystals were filtered and dried to furnish Λ^-acetylcytidine (102 g, 87.0percent).
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 41, p. 7253 - 7254
[2] Patent: CN107033205, 2017, A, . Location in patent: Paragraph 0033; 0034; 0035; 0036
[3] Patent: US6822089, 2004, B1, . Location in patent: Page column 13
[4] Nucleosides and Nucleotides, 1997, vol. 16, # 4, p. 469 - 474
[5] Patent: WO2010/108140, 2010, A1, . Location in patent: Page/Page column 138
[6] Journal of Organic Chemistry, 2002, vol. 67, # 26, p. 9331 - 9339
[7] Journal of the American Chemical Society, 1983, vol. 105, # 12, p. 4059 - 4065
[8] Phosphorus, Sulfur and Silicon and Related Elements, 2002, vol. 177, # 6-7, p. 1783 - 1786
[9] Tetrahedron Letters, 1998, vol. 39, # 14, p. 1897 - 1900
  • 16
  • [ 65-46-3 ]
  • [ 3768-18-1 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 24, p. 2817 - 2820
[2] Bioscience, Biotechnology and Biochemistry, 2000, vol. 64, # 2, p. 363 - 368
[3] Tetrahedron Letters, 1989, vol. 30, # 1, p. 71 - 74
[4] Patent: US5808039, 1998, A,
  • 17
  • [ 64-19-7 ]
  • [ 65-46-3 ]
  • [ 3768-18-1 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 7, p. 2061 - 2064
  • 18
  • [ 70740-24-8 ]
  • [ 65-46-3 ]
  • [ 3768-18-1 ]
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 25, p. 4201 - 4203
  • 19
  • [ 65-46-3 ]
  • [ 121058-88-6 ]
Reference: [1] Tetrahedron Letters, 1989, vol. 30, # 1, p. 71 - 74
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