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[ CAS No. 1032-65-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1032-65-1
Chemical Structure| 1032-65-1
Structure of 1032-65-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1032-65-1 ]

CAS No. :1032-65-1 MDL No. :MFCD00006546
Formula : C9H14N3O7P Boiling Point : -
Linear Structure Formula :- InChI Key :NCMVOABPESMRCP-SHYZEUOFSA-N
M.W : 307.20 Pubchem ID :13945
Synonyms :
2'-Deoxycytidine-5'-monophosphate;Deoxycytidylate;1032-65-1;dCMP

Calculated chemistry of [ 1032-65-1 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.56
Num. rotatable bonds : 4
Num. H-bond acceptors : 8.0
Num. H-bond donors : 4.0
Molar Refractivity : 65.6
TPSA : 166.94 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -10.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.21
Log Po/w (XLOGP3) : -3.42
Log Po/w (WLOGP) : -1.73
Log Po/w (MLOGP) : -2.71
Log Po/w (SILICOS-IT) : -2.52
Consensus Log Po/w : -2.12

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.11

Water Solubility

Log S (ESOL) : 0.45
Solubility : 870.0 mg/ml ; 2.83 mol/l
Class : Highly soluble
Log S (Ali) : 0.49
Solubility : 954.0 mg/ml ; 3.1 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 1.04
Solubility : 3380.0 mg/ml ; 11.0 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.07

Safety of [ 1032-65-1 ]

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
GHS Pictogram:

Application In Synthesis of [ 1032-65-1 ]

* 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 [ 1032-65-1 ]

[ 1032-65-1 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 50-00-0 ]
  • [ 1032-65-1 ]
  • [ 13009-95-5 ]
YieldReaction ConditionsOperation in experiment
in Gegenwart eines Enzympraeparats aus virusinfizierten Escherichiacoli-Zellen;
  • 2
  • [ 1071-23-4 ]
  • [ 1032-65-1 ]
  • [ 30817-64-2 ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-carbodiimide
  • 4
  • 2'-deoxy-[3']cytidylic acid monobenzyl ester [ No CAS ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
With ethanol; water; palladium Hydrogenation;
  • 5
  • [ 512-56-1 ]
  • [ 1032-65-1 ]
  • Phosphoric acid (2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester [ No CAS ]
  • 3-methyldeoxyuridine 5'-phosphate [ No CAS ]
  • 3-methyldeoxyuridine 5'-phosphate methyl ester [ No CAS ]
  • 3-methyldeoxycytidine 5'-phosphate methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 33 % Spectr. 2: 19 % Spectr. 3: 24 % Spectr. 4: 5 % Spectr. In water at 60℃; for 24h; pH=10; Further byproducts given;
1: 8 % Spectr. 2: 4 % Spectr. 3: 83 % Spectr. In water at 60℃; for 72h; pH=10;
  • 6
  • [ 512-56-1 ]
  • [ 1032-65-1 ]
  • Phosphoric acid (2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester [ No CAS ]
  • 3-methyldeoxyuridine 5'-phosphate [ No CAS ]
  • 3-methyldeoxycytidine 5'-phosphate [ No CAS ]
  • 3-methyldeoxycytidine 5'-phosphate methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 5 % Spectr. 2: 19 % Spectr. 3: 5 % Spectr. 4: 33 % Spectr. In water at 60℃; for 24h; pH=10; Further byproducts given;
  • 7
  • [ 512-56-1 ]
  • [ 1032-65-1 ]
  • Phosphoric acid (2R,3S,5R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester methyl ester [ No CAS ]
  • 3-methyldeoxyuridine 5'-phosphate methyl ester [ No CAS ]
  • 3-methyldeoxycytidine 5'-phosphate [ No CAS ]
  • 3-methyldeoxycytidine 5'-phosphate methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 5 % Spectr. 2: 22 % Spectr. 3: 3 % Spectr. 4: 62 % Spectr. In water at 60℃; for 72h; pH=7;
  • 8
  • [ 4715-05-3 ]
  • [ 1032-65-1 ]
  • [ 81788-42-3 ]
YieldReaction ConditionsOperation in experiment
14.5% In N,N-dimethyl-formamide at 25℃; for 0.00555556h;
  • 10
  • C71H97N27O50P8 [ No CAS ]
  • [ 1032-65-1 ]
  • [ 4603-58-1 ]
  • Phosphoric acid (2R,3S,5R)-5-(5-amino-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-phosphonooxymethyl-tetrahydro-furan-3-yl ester 2,3,5-trihydroxy-pentyl ester [ No CAS ]
  • [ 902-04-5 ]
YieldReaction ConditionsOperation in experiment
With alkaline phosphatase; snake venom phosphodiesterase Further byproducts given;
  • 11
  • [ 902-04-5 ]
  • 2'-dC-5'-MP deprotonated radical cation [ No CAS ]
  • [ 1032-65-1 ]
  • 2'-dG-5'-MP deprotonated radical cation [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 20℃; pH = 1;
  • 12
  • C34H47N10O23P3 [ No CAS ]
  • [ 1032-65-1 ]
  • C25H35N7O17P2 [ No CAS ]
  • C25H35N7O16P2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 51% 2: 58% With Tris-borate buffer at 90℃; for 7h;
1: 51% 2: 58% With sodium tetrahydroborate; Tris-borate buffer 1.) 90 deg C, 7 h, 2.) acetonitrile, 0 deg C, 1 h; Yield given. Multistep reaction;
  • 13
  • [ 951-77-9 ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 2'-Deoxycytidine With trichlorophosphate at 20℃; for 0.15h; Flow reactor; Green chemistry; Stage #2: With water at 20℃; Flow reactor; Green chemistry; chemoselective reaction;
78% With tris(p-nitrophenyl)phosphate at 50℃; Erwina herbicola 47/3 cells;
With Tris-HCl buffer; ATP; diothiothreitol In various solvent(s) at 37℃;
With recombinant human deoxycytidine kinase (EC 2.7.1.74); ATP In various solvent(s) at 37℃;
With Tris-HCl buffer; recombinant human cytosolic deoxycytidine kinase; ATP In water; dimethyl sulfoxide at 37℃;
With ATP; magnesium chloride In various solvent(s) at 25℃;
Multi-step reaction with 3 steps 1: pyridine 2: pyridine / und Erwaermen des Reaktionsprodukts mit wss.Essigsaeure 3: palladium; ethanol; water / Hydrogenation
Multi-step reaction with 5 steps 1: pyridine 2: pyridine 3: acetic acid; water 4: pyridine / und Erwaermen des Reaktionsprodukts mit 4-Methyl-morpholin in Benzol 5: palladium; ethanol; water / Hydrogenation
With recombinant human deoxycytidine kinase, His-tagged; potassium chloride; ATP; magnesium chloride; Cleland's reagent; BSA at 37℃; aq. buffer; Enzymatic reaction;
With recombinant deoxyribonucleoside kinase AtdNK from Arabidopsis thaliana (ecotype Columbia); ATP In aq. buffer Enzymatic reaction;
With drosophila melanogaster deoxyribonucleoside kinase; ATP; magnesium chloride In aq. buffer at 37℃; for 24h; Enzymatic reaction;
With potassium chloride; wild-type deoxycytidine kinase; sodium fluoride; ATP; 2-amino-2-hydroxymethyl-1,3-propanediol; magnesium chloride In aq. buffer at 37℃; Enzymatic reaction;

Reference: [1]Zhu, Chenjie; Tang, Chenglun; Cao, Zhi; He, Wei; Chen, Yong; Chen, Xiaochun; Guo, Kai; Ying, Hanjie [Organic Process Research and Development, 2014, vol. 18, # 11, p. 1575 - 1581]
[2]Zinchenko, A. I.; Barai, V. N.; Mikhailopulo, I. A. [Chemistry of Natural Compounds, 1989, vol. 25, # 5, p. 626 - 627][Khimiya Prirodnykh Soedinenii, 1989, vol. 25, # 5, p. 732 - 733]
[3]Gaubert, Gilles; Mathe, Christophe; Imbach, Jean-Louis; Eriksson, Staffan; Vincenzetti, Silvia; Salvatori, Daniela; Vita, Alberto; Maury, Georges [European Journal of Medicinal Chemistry, 2000, vol. 35, # 11, p. 1011 - 1019]
[4]Johansson, Magnus; Karlsson, Anna [Biochemical Pharmacology, 1995, vol. 50, # 2, p. 163 - 168]
[5]Al-Madhoun, Ashraf Said; Eriksson, Staffan; Wang, Zhi-Xian; Naimi, Ebrahim; Knaus, Edward E.; Wiebe, Leonard I. [Nucleosides, nucleotides and nucleic acids, 2004, vol. 23, # 12, p. 1865 - 1874]
[6]Murakami, Eisuke; Bao, Haiying; Ramesh, Mangala; McBrayer, Tamara R.; Whitaker, Tony; Steuer, Holly M. Micolochick; Schinazi, Raymond F.; Stuyver, Lieven J.; Obikhod, Aleksandr; Otto, Michael J.; Furman, Phillip A. [Antimicrobial Agents and Chemotherapy, 2007, vol. 51, # 2, p. 503 - 509]
[7]Michelson; Todd [Journal of the Chemical Society, 1954, p. 34,37]
[8]Michelson; Todd [Journal of the Chemical Society, 1954, p. 34,37]
[9]Location in patent: experimental part Golitsina, Nina L.; Danehy Jr., Francis T.; Fellows, Ross; Cretton-Scott, Erika; Standring, David N. [Antiviral Research, 2010, vol. 85, # 3, p. 470 - 481]
[10]Clausen, Anders R.; Girandon, Lenart; Ali, Ashfaq; Knecht, Wolfgang; Rozpedowska, Elzbieta; Sandrini, Michael P. B.; Andreasson, Erik; Munch-Petersen, Birgitte; Piskur, Jure [FEBS Journal, 2012, vol. 279, # 20, p. 3889 - 3897]
[11]Serra, Immacolata; Conti, Silvia; Piskur, Jure; Clausen, Anders R.; Munch-Petersen, Birgitte; Terreni, Marco; Ubiali, Daniela [Advanced Synthesis and Catalysis, 2014, vol. 356, # 2-3, p. 563 - 570]
[12]Wang, Danyang; Zhang, Yu; Kleiner, Ralph E. [Journal of the American Chemical Society, 2020, vol. 142, # 34, p. 14417 - 14421]
  • 14
  • 4-Methoxy-benzoic acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-2-phosphonooxymethyl-tetrahydro-furan-3-yl ester [ No CAS ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine; ammonium hydroxide at 50℃; for 12h;
  • 15
  • [ 1032-65-1 ]
  • [ 951-77-9 ]
YieldReaction ConditionsOperation in experiment
With cerium(III) chloride; HEPES buffer; oxygen In water at 50℃;
With phosphate buffer; D-glucose; Xantomonas maltophilia at 30℃; for 40h;
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; methanol Hydrolysis;
With perchloric acid; water Hydrolysis;
With water; 2,4,6-Trinitrophenol Hydrolysis;
With sodium hydrogen arsenate; enzyme-substance from of the small intestine-mucous membrane of calf Hydrolysis;

  • 19
  • [ 1032-65-1 ]
  • [ 800-73-7 ]
YieldReaction ConditionsOperation in experiment
With ATP:CMP-phosphotransferase
  • 20
  • [ 1032-65-1 ]
  • 2'-deoxycytidine 5'-triphosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With enzyme-substances from escherichia coli
  • 21
  • [ 1032-65-1 ]
  • [ 800-73-7 ]
YieldReaction ConditionsOperation in experiment
With pyridine; phosphoric acid; dicyclohexyl-carbodiimide
  • 22
  • [ 1032-65-1 ]
  • 2'-deoxycytidine 5'-triphosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; phosphoric acid; dicyclohexyl-carbodiimide unter Zusatz von Tributylamin;
  • 23
  • [ 1032-65-1 ]
  • 2'-deoxycytidine 5'-triphosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; phosphoric acid; dicyclohexyl-carbodiimide
  • 24
  • [ 1032-65-1 ]
  • [ 6094-83-3 ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-carbodiimide
  • 25
  • [ 58781-41-2 ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide In water at 65℃; for 6h;
  • 26
  • [ 265137-12-0 ]
  • [ 64395-31-9 ]
  • [ 1032-65-1 ]
  • 2'-isodeoxy-adenosine 3'-monophosphate [ No CAS ]
  • [ 951-77-9 ]
YieldReaction ConditionsOperation in experiment
With phosphodiesterase I In various solvent(s) at 37℃; for 1h; Enzymatic reaction;
  • 27
  • [ 1032-65-1 ]
  • [ 800-73-7 ]
YieldReaction ConditionsOperation in experiment
With pyrimidine nucleoside monophosphate kinase (EC 2.7.4.14.) In phosphate buffer at 37℃;
  • 28
  • [ 23339-46-0 ]
  • [ 1032-65-1 ]
  • [ 958-09-8 ]
YieldReaction ConditionsOperation in experiment
With acetate buffer; bovine spleen phosphodiesterase II at 37℃; for 1h;
  • 29
  • [ 265137-12-0 ]
  • [ 64395-31-9 ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
With acetate buffer; bovine spleen phosphodiesterase II at 37℃; for 1h;
YieldReaction ConditionsOperation in experiment
Multistep reaction;
  • 31
  • [ 39968-33-7 ]
  • [ 1032-65-1 ]
  • [ 872003-30-0 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In water at 20℃; for 2h;
  • 32
  • C12H27N*C9H16N3O13P3 [ No CAS ]
  • [ 1032-65-1 ]
  • C18H28N6O19P4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: cytidine 5'-(dihydrogen phosphate) With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: C12H27N*C9H16N3O13P3 In N,N-dimethyl-formamide at 20℃;
  • 33
  • [ 17182-39-7 ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: TPS-TAZ / pyridine / 2 h / 25 °C 2: NH4OH / H2O / 1 h / 25 °C 3: NH4OH / H2O / 6 h / 65 °C
  • 34
  • Phosphoric acid (2R,3S,5R)-5-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester 2-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethanesulfonyl}-ethyl ester [ No CAS ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NH4OH / H2O / 1 h / 25 °C 2: NH4OH / H2O / 6 h / 65 °C
  • 35
  • d(GTAC) [ No CAS ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 0.5 percent / acetonitrile; H2O / 15 h / 0 °C 2: 100 percent / H2O / 0.08 h / 90 °C 3: 51 percent / 1.) Tris-borate buffer, 2.) NaBH4 / 1.) 90 deg C, 7 h, 2.) acetonitrile, 0 deg C, 1 h
  • 36
  • [ 1032-65-1 ]
  • [ 81788-47-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 14.5 percent / dimethylformamide / 0.01 h / 25 °C 2: sodium methoxide / methanol; H2O / 48 h / Ambient temperature
  • 37
  • [ 70284-47-8 ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / und Erwaermen des Reaktionsprodukts mit 4-Methyl-morpholin in Benzol 2: palladium; ethanol; water / Hydrogenation
  • 38
  • [ 18531-20-9 ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / und Erwaermen des Reaktionsprodukts mit wss.Essigsaeure 2: palladium; ethanol; water / Hydrogenation
Multi-step reaction with 4 steps 1: pyridine 2: acetic acid; water 3: pyridine / und Erwaermen des Reaktionsprodukts mit 4-Methyl-morpholin in Benzol 4: palladium; ethanol; water / Hydrogenation
  • 39
  • [ 70284-43-4 ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: acetic acid; water 2: pyridine / und Erwaermen des Reaktionsprodukts mit 4-Methyl-morpholin in Benzol 3: palladium; ethanol; water / Hydrogenation
  • 40
  • [ 39968-33-7 ]
  • [ 1032-65-1 ]
  • HATU [ No CAS ]
  • [ 872003-30-0 ]
YieldReaction ConditionsOperation in experiment
29% Stage #1: 1-hydroxy-7-aza-benzotriazole; cytidine 5'-(dihydrogen phosphate); HATU With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With sodium perchlorate In diethyl ether; N,N-dimethyl-formamide; acetone at 0℃; for 0.333333h; 1 Examples1. Synthesis of l-(2 '-Deoxycytidine-5 '-O-phosphor-5' -P-yl)-2-azabenzotriazolide 2'-Deoxycytidine-5?-monophosphate (124 ?mol, 40 mg) in 5 ml DMF was treated with 1- hydroxy-7-azabenzotriazole (248 ?mol, 33.6 mg), O-(7-azaberizotriazol-l-yl)-A?N,.?f'',iV''- tetramethyluronium hexafluorophosphate (248 ?mol, 94.4 mg) and diisopropylethylamine (32 ?l, 186 ?mol). The suspension was stirred 1 h at room temperature under argon. The product was then precipitated by adding to an icecold solution Of NaClO4 (46 mg, 0.38 mmol) in dry acetone (23.4 ml) and dry diethylether (14.6 ml). After stirring for 20 min at 0C, the precipitate was isolated by centrifugation. The solid was washed two times with acetone/Et2O (1:1, v/v, 10 ml) and two times with acetone (10 ml). After drying at 0.1 Torr overnight, the azabenzotriazolide title compound was obtained as pale yellow solid. It was stored under argon at -80C until usage. Yield: 29 % 31P NMR (500 MHZ, DMSO-d6) ? = -0.86 ppm.
  • 41
  • [ 288-88-0 ]
  • [ 1032-65-1 ]
  • 1-(2'-deoxycytidine-5'-0-phosphor-5'-P-yl)-2-triazolide [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% Stage #1: 1,2,4-Triazole; cytidine 5'-(dihydrogen phosphate) With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With sodium perchlorate In diethyl ether; N,N-dimethyl-formamide; acetone at 0℃; for 0.333333h; 2 2. Synthesis of l-(2'-Deoxycytidine-5'-0-phosphor-5x-P-yl)-2-triazolideA slurry of 2 '-deoxycytidine-5" -monophosphate (77 ?mol, 25 mg) in 500 ?l DMF was treated with 1,2,4-iH-triazole (385 ?mol, 26,6 mg), triethylamine (65 ?l, 462 ?mol), triphenylphosphine(65 mg, 246,5 ?mol) and 2,2'-dipyridyldisuflide (54 mg, 246,5 ?mol). The suspension was stirred for 1 h at room temperature under argon until all monophosphate is dissolved. The product was then precipitated by adding to an ice-cold solution Of NaClO4 (46 mg, 0.38 mmol) in dry acetone (23.4 ml) and dry diethylether (14.6 ml). After stirring for 20 min at 0 C, the precipitate was isolated by centrifugation. The solid was washed twice with acetone/Et2O (1:1, vZv, 10 ml) and twice with acetone (10 ml). After drying at 0.1 Torr for 16 h, the nucleotidic triazolide was obtained as colourless solid. It was stored under argon at -80C until usage.Yield: 43 %, TLC (cellulose) (1PrOHZNH3ZH2O 7:1:2) Rf= 0.5 31P NMR (202,4 MHz, DMSO-d6) ? = -11.4, - 12.6 ppm.
  • 42
  • [ 1032-65-1 ]
  • [ 35763-29-2 ]
  • P1-(2-thiouridine-5'-)-P4-(2'-deoxycytidine-5'-)-tetraphosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-thio-1-β-D-ribofuranosyl(3H)pyrimidine-2,4-dione 5'-triphosphate With tributyl-amine; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: cytidine 5'-(dihydrogen phosphate) With tributyl-amine In N,N-dimethyl-formamide at 20℃; for 48h; Further stages.;
  • 43
  • [ 39968-33-7 ]
  • [ 1032-65-1 ]
  • C14H15N7O7P(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-hydroxy-7-aza-benzotriazole; cytidine 5'-(dihydrogen phosphate) With N-ethyl-N,N-diisopropylamine; HATU In 1-methyl-pyrrolidin-2-one Stage #2: With sodium perchlorate In 1-methyl-pyrrolidin-2-one; diethyl ether; acetone
  • 44
  • [ 693-98-1 ]
  • [ 1032-65-1 ]
  • C13H17N5O6P(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-methylimidazole; cytidine 5'-(dihydrogen phosphate) With 2,2'-dipyridyldisulphide; triethylamine; triphenylphosphine In dimethyl sulfoxide Stage #2: With sodium perchlorate In diethyl ether; dimethyl sulfoxide; acetone
  • 45
  • plutonium(IV) nitrate [ No CAS ]
  • [ 1032-65-1 ]
  • [Pu(IV)4(NO3)8(deoxycytidinemonophosphate)4(H2O)8](NO3)4*2H2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; nitric acid aq. HNO3; ligand dissolved in H2O, soln. of Pu(NO3)4 in aq. HNO3 added, isothermally evapd. at 20°C;
  • 46
  • [ 1032-65-1 ]
  • [β-(32)P]dCDP [ No CAS ]
YieldReaction ConditionsOperation in experiment
With T5 bacteriophage deoxynucleoside monophosphate kinase; potassium chloride; ATP; ATP; magnesium chloride at 37℃; Tris-HCl buffer; Enzymatic reaction;
  • 47
  • C77H101N26O47P7 [ No CAS ]
  • [ 1032-65-1 ]
  • C86H113N29O53P8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
99 %Spectr. With 1-methyl-1H-imidazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium chloride at 10℃; for 168h; aq. buffer;
  • 48
  • [ 1093283-46-5 ]
  • [ 5204-74-0 ]
  • [ 1032-65-1 ]
  • [ 25952-53-8 ]
  • C76H98N33O43P7 [ No CAS ]
  • C69H88N30O38P6 [ No CAS ]
  • C75H103N33O37P6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 69 %Spectr. 2: 13 %Spectr. 3: 10 %Spectr. Stage #1: 5'-d(CGCACG(2',3'-dideoxy-3'-amino-A))-3'; cytidine 5'-(dihydrogen phosphate); 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride With 1-methyl-1H-imidazole; sodium chloride at 10℃; for 168h; aq. buffer; Stage #2: triethylammonium acetate aq. buffer;
1: 27 %Spectr. 2: 13 %Spectr. 3: 7 %Spectr. Stage #1: 5'-d(CGCACG(2',3'-dideoxy-3'-amino-A))-3'; cytidine 5'-(dihydrogen phosphate); 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride With 1-methyl-1H-imidazole; sodium chloride at 10℃; for 168h; aq. buffer; Stage #2: triethylammonium acetate aq. buffer;
  • 49
  • [ 1093283-46-5 ]
  • [ 1032-65-1 ]
  • C76H98N33O43P7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
> 99 %Spectr. With 1-methyl-1H-imidazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium chloride; magnesium chloride at 10℃; for 168h; aq. buffer;
  • 50
  • 5'-CACTGACTGTATG-3' [ No CAS ]
  • [ 1032-65-1 ]
  • 5'-CACTGACTGTATGC-3' [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 5'-CTCGTCAGCATCTTCAGCATACAGTCAGTG-3'; recombinant human REV1 polymerase (341-829) at 30℃; aq. buffer; Enzymatic reaction;
  • 51
  • [ 1268154-58-0 ]
  • [ 1032-65-1 ]
  • [ 1309478-74-7 ]
YieldReaction ConditionsOperation in experiment
6% With triethylamine In N,N-dimethyl-formamide at 20℃; for 120h; Inert atmosphere;
  • 52
  • [ 3518-85-2 ]
  • [ 1032-65-1 ]
  • C17H27N4O10P [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; dicyclohexyl-carbodiimide In 1,4-dioxane; N,N-dimethyl-formamide at 85℃; for 3h; Inert atmosphere;
  • 53
  • [ 3518-85-2 ]
  • [ 1032-65-1 ]
  • [ 1331741-07-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; dicyclohexyl-carbodiimide / 1,4-dioxane; N,N-dimethyl-formamide / 3 h / 85 °C / Inert atmosphere 2: sodium hydroxide / methanol; water / 1.5 h / 20 °C
  • 54
  • [ 39987-25-2 ]
  • [ 1032-65-1 ]
  • C15H23N4O10P [ No CAS ]
  • 55
  • [ 1032-65-1 ]
  • [ 1254159-43-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; dicyclohexyl-carbodiimide / 1,4-dioxane; N,N-dimethyl-formamide / 3 h / 85 °C / Inert atmosphere 2: sodium hydroxide / methanol; water / 1.5 h / 20 °C
  • 56
  • [ 1378466-30-8 ]
  • [ 1032-65-1 ]
  • C9H14N3O7P*C44H34N2O8P2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; acetonitrile
  • 57
  • C49H55N7O19P2 [ No CAS ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
With water; sodium hydroxide at 60℃; for 6h;
  • 58
  • C39H52N13O23P3 [ No CAS ]
  • [ 1363821-18-4 ]
  • [ 1032-65-1 ]
YieldReaction ConditionsOperation in experiment
With water; sodium hydroxide at 60℃; for 4h;
  • 59
  • [ 1032-65-1 ]
  • [ 1342261-58-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: iodic acid 2.1: copper(l) iodide / N,N-dimethyl-formamide / Inert atmosphere; Darkness 2.2: 18 h / 20 °C / Inert atmosphere; Darkness
  • 60
  • [ 1032-65-1 ]
  • C15H22N4O14P3(3-)*3Li(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: iodic acid 2.1: copper(l) iodide / N,N-dimethyl-formamide / Inert atmosphere; Darkness 2.2: 18 h / 20 °C / Inert atmosphere; Darkness 3.1: tributyl-amine / water; dimethyl sulfoxide; acetonitrile 4.1: ammonia; water / dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile
  • 61
  • [ 1032-65-1 ]
  • C17H21F3N4O15P3(3-)*3Li(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: iodic acid 2.1: copper(l) iodide / N,N-dimethyl-formamide / Inert atmosphere; Darkness 2.2: 18 h / 20 °C / Inert atmosphere; Darkness 3.1: tributyl-amine / water; dimethyl sulfoxide; acetonitrile
  • 62
  • [ 1032-65-1 ]
  • C31H50N7O17P3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: iodic acid 2.1: copper(l) iodide / N,N-dimethyl-formamide / Inert atmosphere; Darkness 2.2: 18 h / 20 °C / Inert atmosphere; Darkness 3.1: tributyl-amine / water; dimethyl sulfoxide; acetonitrile 4.1: water; sodium hydrogencarbonate; sodium carbonate / pH 9 4.2: 1.5 h
Multi-step reaction with 5 steps 1.1: iodic acid 2.1: copper(l) iodide / N,N-dimethyl-formamide / Inert atmosphere; Darkness 2.2: 18 h / 20 °C / Inert atmosphere; Darkness 3.1: tributyl-amine / water; dimethyl sulfoxide; acetonitrile 4.1: ammonia; water / dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile 5.1: dimethyl sulfoxide / 1.5 h
  • 64
  • 5'-d(CAGCT<SUB>PMe</SUB>G), PMe = methylphosphonate link [ No CAS ]
  • 5'-d(pT<SUB>PMe</SUB>G), PMe = methylphosphonate link [ No CAS ]
  • [ 1032-65-1 ]
  • [ 653-63-4 ]
  • [ 902-04-5 ]
  • [ 951-77-9 ]
YieldReaction ConditionsOperation in experiment
With nuclease P1 from Penicillium citrinum at 37℃; for 0.0833333h; Enzymatic reaction;
  • 65
  • [ 1032-65-1 ]
  • [ 71-30-7 ]
YieldReaction ConditionsOperation in experiment
With MilB wild type hydrolase; water In aq. buffer at 37℃; for 0.5h; Enzymatic reaction;
  • 66
  • [ 2052-49-5 ]
  • [ 1032-65-1 ]
  • C9H12N3O7P(2-)*2C16H36N(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water Inert atmosphere;
  • 67
  • [ 1032-65-1 ]
  • δ-(4-methyl-7-coumarinyl) 2′-deoxycytosine 5′-tetraphosphate tetraammonium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: water / pH 7.0 / Inert atmosphere 2: magnesium chloride / acetonitrile; N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere 3: Dowex-50-W ion-exchange resin NH4+ form / Inert atmosphere
  • 68
  • [ 1032-65-1 ]
  • C19H19N3O18P4(4-)*4C16H36N(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water / pH 7.0 / Inert atmosphere 2: magnesium chloride / acetonitrile; N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere
  • 69
  • [ 1032-65-1 ]
  • C10H18N3O12P3*3C12H27N [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dicyclohexyl-carbodiimide / water; <i>tert</i>-butyl alcohol 2.1: water; ethanol 2.2: 20 °C
  • 71
  • [ 1032-65-1 ]
  • [ 99-98-9 ]
  • dCMP-DMPA [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1H-imidazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; acetonitrile
  • 72
  • [ 50-00-0 ]
  • [ 1032-65-1 ]
  • (4-hydroxymethyl)deoxycytidine monophosphate [ No CAS ]
  • (4-dihydroxymethyl)deoxycytidine monophosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water-d2 at 37℃;
  • 73
  • [ 1032-65-1 ]
  • C17H22BrN4O14P3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere
  • 74
  • [ 1032-65-1 ]
  • C17H22BrN4O14P3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere
  • 75
  • [ 1032-65-1 ]
  • C17H22ClN4O14P3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere
  • 76
  • [ 1032-65-1 ]
  • C17H22ClN4O14P3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere
  • 77
  • [ 1032-65-1 ]
  • C17H22FN4O14P3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere
  • 78
  • [ 1032-65-1 ]
  • C17H22FN4O14P3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere
  • 79
  • [ 1032-65-1 ]
  • [(R)-[([(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}(bromo)methyl]phosphonic acid triethylammonium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere 3: water / 48 h / Irradiation
  • 80
  • [ 1032-65-1 ]
  • [(S)-[([(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}(bromo)methyl]phosphonic acid triethylammonium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere 3: water / 48 h / Irradiation
  • 81
  • [ 1032-65-1 ]
  • [(R)-[([(2R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}(chloro)methyl]phosphonic acid triethylammonium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere 3: water / 48 h / Irradiation
  • 82
  • [ 1032-65-1 ]
  • [(S)-[([(2R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}(chloro)methyl]phosphonic acid triethylammonium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere 3: water / 48 h / Irradiation
  • 83
  • [ 1032-65-1 ]
  • [(R)-[([(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}(fluoro)methyl]phosphonic acid triethylammonium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere 3: water / 48 h / Irradiation
  • 84
  • [ 1032-65-1 ]
  • [(S)-[([(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}(fluoro)methyl]phosphonic acid triethylammonium salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-carbodiimide / <i>tert</i>-butyl alcohol 2: dimethyl sulfoxide / 20 °C / Inert atmosphere 3: water / 48 h / Irradiation
  • 85
  • [ 643755-84-4 ]
  • [ 1032-65-1 ]
  • C30H28N3O10P [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide In water; <i>tert</i>-butyl alcohol for 2h; Reflux;
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