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Chemical Structure| 838-07-3 Chemical Structure| 838-07-3
Chemical Structure| 838-07-3

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5-Methyl-2'-deoxycytidine (5-Me-dC) is a minor component found in most eukaryotic DNA.

Synonyms: 5-Methyldeoxycytidine

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Product Details of 5-Methyl-2'-deoxycytidine

CAS No. :838-07-3
Formula : C10H15N3O4
M.W : 241.24
SMILES Code : CC1=CN([C@H]2C[C@H](O)[C@@H](CO)O2)C(=O)N=C1N
Synonyms :
5-Methyldeoxycytidine
MDL No. :MFCD00006549
InChI Key :LUCHPKXVUGJYGU-XLPZGREQSA-N
Pubchem ID :440055

Safety of 5-Methyl-2'-deoxycytidine

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 5-Methyl-2'-deoxycytidine

* 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 [ 838-07-3 ]
  • Downstream synthetic route of [ 838-07-3 ]

[ 838-07-3 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 50-89-5 ]
  • [ 838-07-3 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: With 1,8-diazabicyclo[5.4.0]undec-7-ene; ((3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) In N,N-dimethyl-formamide at 20℃; for 0.0166667 h;
Stage #2: With ammonium hydroxide In N,N-dimethyl-formamide at 20℃; for 2 h;
General procedure: To a solution of the nucleosides (2–20) in DMF ([substrate]=0.3M, except for 3 and 4, [3,4]=0.05M) were added PyAOP (1.6 eq) and DBU (1.6 eq). The reaction was stirred at 20°C for 1min. To the reaction solution was added N-nucleophiles (4 eq) (or 1a in THF, conc. NH4OH (10 eq)). The reaction was stirred at 20°C for 5min−4h and monitored by TLC. Upon completion, the solution was concentrated in vacuo. Flash column chromatography on silica gel afforded 5MedC and oxidized 5MedC derivatives (1′–20′) in pure form.
References: [1] Tetrahedron, 2018, vol. 74, # 49, p. 7095 - 7101.
[2] Nucleosides and Nucleotides, 1996, vol. 15, # 4, p. 907 - 921.
[3] Journal of the American Chemical Society, 1959, vol. 81, p. 178,187.
  • 2
  • [ 115652-25-0 ]
  • [ 838-07-3 ]
References: [1] Tetrahedron, 1996, vol. 52, # 19, p. 6759 - 6780.
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 21, p. 3053 - 3054.
  • 3
  • [ 80991-41-9 ]
  • [ 838-07-3 ]
References: [1] Journal of the Chemical Society, Chemical Communications, 1981, # 20, p. 1089.
  • 4
  • [ 80991-42-0 ]
  • [ 838-07-3 ]
References: [1] Angewandte Chemie - International Edition, 2010, vol. 49, # 31, p. 5375 - 5377.
  • 5
  • [ 93841-35-1 ]
  • [ 838-07-3 ]
References: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 178,187.
[2] Biochemical Preparations, 1963, vol. 10, p. 98,102.
  • 6
  • [ 3226-65-1 ]
  • [ 951-77-9 ]
  • [ 838-07-3 ]
References: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 260 - 265.
  • 7
  • [ 67-68-5 ]
  • [ 951-77-9 ]
  • [ 838-07-3 ]
References: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 260 - 265.
  • 8
  • [ 50-89-5 ]
  • [ 838-07-3 ]
References: [1] Gazzetta Chimica Italiana, 1983, vol. 113, # 11/12, p. 863 - 864.
  • 9
  • [ 35898-30-7 ]
  • [ 838-07-3 ]
References: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 178,187.
  • 10
  • [ 20188-74-3 ]
  • [ 838-07-3 ]
References: [1] Tetrahedron, 1996, vol. 52, # 19, p. 6759 - 6780.
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 21, p. 3053 - 3054.
  • 11
  • [ 176755-83-2 ]
  • [ 838-07-3 ]
References: [1] Nucleosides and Nucleotides, 1997, vol. 16, # 7-9, p. 1271 - 1278.
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 6, p. 519 - 524.
[3] Indian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry, 1997, vol. 36, # 6, p. 519 - 524.
  • 12
  • [ 10457-18-8 ]
  • [ 838-07-3 ]
References: [1] Nucleosides and Nucleotides, 1996, vol. 15, # 4, p. 907 - 921.
  • 13
  • [ 6979-97-1 ]
  • [ 838-07-3 ]
References: [1] Journal of the Chemical Society, Chemical Communications, 1981, # 20, p. 1089.
  • 14
  • [ 91290-54-9 ]
  • [ 838-07-3 ]
References: [1] Gazzetta Chimica Italiana, 1983, vol. 113, # 11/12, p. 863 - 864.
  • 15
  • [ 6979-97-1 ]
  • [ 838-07-3 ]
References: [1] Gazzetta Chimica Italiana, 1983, vol. 113, # 11/12, p. 863 - 864.
  • 16
  • [ 2498-41-1 ]
  • [ 838-07-3 ]
References: [1] Journal of Biological Chemistry, 1957, vol. 226, p. 631,633.
 

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