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Chemical Structure| 146954-75-8 Chemical Structure| 146954-75-8
Chemical Structure| 146954-75-8

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DMT-2′Fluoro-dU Phosphoramidite is a fluorinated nucleotide phosphoramidite monomer used for synthesizing highly stable oligonucleotides.

Synonyms: 2'-F-dU Phosphoramidite

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Product Details of DMT-2′Fluoro-dU Phosphoramidite

CAS No. :146954-75-8
Formula : C39H46FN4O8P
M.W : 748.78
SMILES Code : CC(N(C(C)C)P(O[C@@H]1[C@@H](COC(C2=CC=C(OC)C=C2)(C3=CC=C(OC)C=C3)C4=CC=CC=C4)O[C@@H](N(C(N5)=O)C=CC5=O)[C@@H]1F)OCCC#N)C
Synonyms :
2'-F-dU Phosphoramidite
MDL No. :MFCD11113919
InChI Key :HQHQPAYRJJMYQX-DJTPZYMWSA-N
Pubchem ID :9810693

Safety of DMT-2′Fluoro-dU Phosphoramidite

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

Application In Synthesis of DMT-2′Fluoro-dU Phosphoramidite

* 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 [ 146954-75-8 ]

[ 146954-75-8 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 102691-36-1 ]
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YieldReaction ConditionsOperation in experiment
67.3% With 1H-tetrazole; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere 5’-O-(4,4’-Dimethoxytrityl)-2’-deoxy-2’-fluorouridine (3.00 g, 5.47 mmol) obtained in Preparation Example 27-(1)was dissolved in anhydrous dichloromethane (50 ml) under an argon atmosphere, N,N-diisopropylethylamine (0.55 ml,3.18 mmol), 1H-tetrazole (0.45 g, 6.45 mmol) and 2-cyanoethyl-N,N,N’,N’-tetraisopropylphosphordiamidite (1.92 g, 6.36mmol) were added, and the mixture was stirred at room temperature overnight. The completion of the reaction wasconfirmed, 5percent aqueous sodium hydrogen carbonate solution (20 ml) was added to the reaction mixture to allow layerseparation, and the organic layer was washed with saturated brine (20 ml). The organic layer was dried over sodiumsulfate, the filtrate was concentrated and the obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=75:25 - 30/70(v/v), containing 3percent triethylamine). The object fractions were collected and concentratedto give the title compound (2.76 g, 67.3percent).
References: [1] Patent: EP2816053, 2014, A1, . Location in patent: Paragraph 0371.
[2] Patent: US9371353, 2016, B2, . Location in patent: Page/Page column 78.
  • 2
  • [ 146954-74-7 ]
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References: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 7, p. 831 - 841.
  • 3
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References: [1] Helvetica Chimica Acta, 1997, vol. 80, # 6, p. 1952 - 1971.
  • 4
  • [ 40615-36-9 ]
  • [ 146954-75-8 ]
References: [1] Helvetica Chimica Acta, 1997, vol. 80, # 6, p. 1952 - 1971.
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 7, p. 831 - 841.
  • 5
  • [ 56287-17-3 ]
  • [ 146954-75-8 ]
References: [1] Helvetica Chimica Acta, 1997, vol. 80, # 6, p. 1952 - 1971.
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 7, p. 831 - 841.
  • 6
  • [ 40615-36-9 ]
  • [ 56287-17-3 ]
  • [ 146954-75-8 ]
References: [1] Patent: EP2816053, 2014, A1, .
[2] Patent: US9371353, 2016, B2, .
 

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