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Inhibitors/Agonists
Cell Cycle
Nucleoside Antimetabolite/Analog
N2,2'-O-Dimethylguanosine
Inhibitors/Agonists
Cell Cycle
DNA Damage
Nucleoside Antimetabolite/Analog

[ CAS No. 135023-21-1 ] {[proInfo.proName]}

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Chemical Structure| 135023-21-1
Chemical Structure| 135023-21-1
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Quality Control of [ 135023-21-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 135023-21-1 ]

CAS No. :135023-21-1 MDL No. :MFCD28343597
Formula : C12H17N5O5 Boiling Point : -
Linear Structure Formula :- InChI Key :OJTAZBNWKTYVFJ-IOSLPCCCSA-N
M.W : 311.29 Pubchem ID :136381024
Synonyms :
Chemical Name :9-((2R,3R,4R,5R)-4-Hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-2-(methylamino)-1,9-dihydro-6H-purin-6-one

Safety of [ 135023-21-1 ]

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 [ 135023-21-1 ]

* 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 [ 135023-21-1 ]

[ 135023-21-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 2140-71-8 ]
  • [ 135023-21-1 ]
Reference： [1]Patent: WO2014/93924,2014,A1
[2]Patent: WO2015/196130,2015,A2
[3]Patent: WO2015/196128,2015,A2
[4]Patent: EP2918275,2015,A1
  • 2
  • [ 1415223-97-0 ]
  • [ 135023-21-1 ]
Reference： [1]Patent: WO2014/93924,2014,A1
[2]Patent: WO2015/196130,2015,A2
[3]Patent: WO2015/196128,2015,A2
[4]Patent: EP2918275,2015,A1
  • 3
  • [ 1613530-50-9 ]
  • [ 135023-21-1 ]
YieldReaction ConditionsOperation in experiment
43% Sodium borohydride (0.7 g, 18.0 mmol) was added to a solution of compound 175 (3.0 g, 5.8 mmol) in dimethyl sulfoxide (15 m L). The reaction mixture was heated at 100 C for 1 -2 hr, and then cooled to room temperature. It was then quenched with acetic acid/ethanol (50 m l_, v : v = 1 :1 0). The resulted colorless precipitate was filtrated out, and washed thoroughly with methanol. The crude product was dried under reduced pressure, and water was added. After further evaporation of water, the residue was crystallized from water to give N2, 2'-dimethylguanosine 177 as a white solid (0.62 g, 43%). HPLC purity: 98 %, ESI mass spectrum m/z 312.8 [M + H]+ , 623 [2M + 1 ]+, 1 H NMR (300MHz, DMSO-d6) δ 1 .85 (br, 1 H ), 7.93 (s, 1 H), 7.60( br, 1 H), 5.84 (d, J = 3.9Hz, 1 H ), 4.82- 5.10 (br, 2H), 4.26-4.29 (m , 2H), 3.90 (s, 1 H), 3.53-3.57 (m , 2H), 3.35(s, 3H), 2.78 (s, 3H). ESI mass spectrum m/z 312 (M + H)+, 623 (2M + H)+. UV, -max = 258 nm.
43% Synthesis of Compound 1 77: Sodium borohydride (0.7 g, 1 8.0 mmol) was added to a solution of mpound 175 (3.0 g, 5.8 mmol) in dimethyl sulfoxide (15 mL). The reaction mixture was heated at 1 00 for 1 -2 hr, and then cooled to room temperature. It was then quenched with acetic acid/ethanol (50 , v : v = 1 : 1 0). The resulted colorless precipitate was filtrated out, and washed thoroughly with thanol. The crude product was dried under reduced pressure, and water was added. After further aporation of water the residue was crystallized from water to give N2 2' dimethylguanosine 177 as a te solid ( H NMR (300M .10 (br, 2H), 4.26-4.29 (m, 2H), 3.90 (s, 1 H), 3.53-3.57 (m, 2H), 3.35(s, 3H), 2.78 (s, 3H). ESI mass ectrum m/z 312 (M + H)+, 623 (2M + H)+. UV, max = 258 nm.
Reference： [1]Patent: WO2014/93924,2014,A1 .Location in patent: Page/Page column 297; 298
[2]Patent: WO2015/196128,2015,A2 .Location in patent: Page/Page column 638; 639
[3]Patent: WO2015/196130,2015,A2
[4]Patent: EP2918275,2015,A1
  • 4
  • C16H21N5O7 [ No CAS ]
  • [ 135023-21-1 ]
YieldReaction ConditionsOperation in experiment
0.62 g With acetic acid; Synthesis of Compound 1 77: Sodium borohydride (0.7 g, 18.0 mmol) was added to a solution of compound 175 (3.0 g, 5.8 mmol) in dimethyl sulfoxide (15 mL). The reaction mixture was heated at 100 cc for 1-2 hr, and then cooled to room temperature. It was then quenched with acetic acid/ethanol (50mL, v: v = 1:10). The resulted colorless precipitate was filtrated out, and washed thoroughly withmethanol. The crude product was dried under reduced pressure, and water was added. After furtherevaporation of water, the residue was crystallized from water to give N2, 2’-dimethylguanosine 177 as a white solid (0.62 g, 43%). HPLC purity: 98%, ESI mass spectrum m/z312.8 [M + H], 623 [2M + 1], H NMR (300MHz, DMSO-d6) ö 11.85 (br, 1 H), 7.93 (s, 1 H), 7.60( br, 1 H), 5.84 (d, J= 3.9Hz, 1 H ), 4.82-5.10 (br, 2H), 4.26-4.29(m, 2H), 3.90(s, 1H), 3.53-3.57(m, 2H), 3.35(s, 3H), 2.78 (s, 3H). ESI mass spectrum mlz 312 (M + H), 623 (2M + H). UV, max = 258 nm.
0.62 g With acetic acid; In ethanol; Synthesis of Compound 177: Sodium borohydride (0.7 g, 18.0 mmol) was added to a solution of compound 175 (3.0 g, 5.8 mmol) in dimethyl sulfoxide (15 mL). The reaction mixture was heated at 100 C for 1-2 hr, and then cooled to room temperature. It was then quenched with acetic acid/ethanol (50 mL, v : v = 1:10). The resulted colorless precipitate was filtrated out, and washed thoroughly with methanol. The crude product was dried under reduced pressure, and water was added. After further evaporation of water, the residue was crystallized from water to give N2, 2'-dimethylguanosine 177 as a white solid (0.62 g, 43%). HPLC purity: 98 %, ESI mass spectrum m/z 312.8 [M + H]+ , 623 [2M + 1]+, 1H NMR (300MHz, DMSO-d6) δ 11.85 (br, 1H ), 7.93 (s, 1 H), 7.60 ( br, 1 H), 5.84 (d, J = 3.9Hz, 1H ), 4.82-5.10 (br, 2H), 4.26-4.29 (m, 2H), 3.90 (s, 1H), 3.53-3.57 (m, 2H), 3.35(s, 3H), 2.78 (s, 3H). ESI mass spectrum m/z 312 (M + H)+, 623 (2M + H)+. UV, □max = 258 nm.
Reference： [1]Patent: WO2015/196130,2015,A2 .Location in patent: Page/Page column 630; 631
[2]Patent: EP2918275,2015,A1 .Location in patent: Paragraph 2200; 2203
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