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[ CAS No. 2140-79-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 2140-79-6
Chemical Structure| 2140-79-6
Chemical Structure| 2140-79-6
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Product Details of [ 2140-79-6 ]

CAS No. :2140-79-6 MDL No. :
Formula : C11H15N5O4 Boiling Point : -
Linear Structure Formula :- InChI Key :FPUGCISOLXNPPC-IOSLPCCCSA-N
M.W : 281.27 Pubchem ID :102213
Synonyms :
Chemical Name :(2R,3R,4R,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-methoxytetrahydrofuran-3-ol

Calculated chemistry of [ 2140-79-6 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.55
Num. rotatable bonds : 3
Num. H-bond acceptors : 7.0
Num. H-bond donors : 3.0
Molar Refractivity : 67.4
TPSA : 128.54 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) : -8.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.24
Log Po/w (XLOGP3) : -0.51
Log Po/w (WLOGP) : -1.64
Log Po/w (MLOGP) : -2.02
Log Po/w (SILICOS-IT) : -1.89
Consensus Log Po/w : -0.96

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.4
Solubility : 11.3 mg/ml ; 0.04 mol/l
Class : Very soluble
Log S (Ali) : -1.72
Solubility : 5.34 mg/ml ; 0.019 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.29
Solubility : 145.0 mg/ml ; 0.514 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.01

Safety of [ 2140-79-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2140-79-6 ]

* 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 [ 2140-79-6 ]

[ 2140-79-6 ] Synthesis Path-Downstream   1~88

  • 3
  • [ 28920-43-6 ]
  • [ 2140-79-6 ]
  • [ 135944-25-1 ]
  • 2'-O-methyl-6-bis-N-(9-fluorenylmethoxycarbonyl)adenosine [ No CAS ]
  • 5
  • [ 17287-03-5 ]
  • [ 2140-79-6 ]
  • [ 57817-83-1 ]
  • [ 20649-46-1 ]
  • [ 91101-00-7 ]
  • [ 30891-53-3 ]
  • 6
  • [ 2140-79-6 ]
  • [ 92611-10-4 ]
  • 2'-O-methyl-cis-adenosine 3',5'-cyclic methyl monophosphite [ No CAS ]
  • 8
  • [ 512-56-1 ]
  • [ 58-61-7 ]
  • [ 57817-83-1 ]
  • [ 2140-79-6 ]
  • [ 1867-73-8 ]
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  • 9
  • [ 512-56-1 ]
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  • 10
  • [ 17287-03-5 ]
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  • [ 15763-06-1 ]
  • 11
  • [ 17287-03-5 ]
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  • [ 1867-73-8 ]
  • [ 2620-62-4 ]
  • 12
  • [ 17287-03-5 ]
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  • [ 1867-73-8 ]
  • [ 10300-22-8 ]
  • 15
  • [ 17287-03-5 ]
  • [ 58-61-7 ]
  • [ 57817-83-1 ]
  • [ 20649-46-1 ]
  • [ 2140-79-6 ]
  • [ 10300-22-8 ]
  • 16
  • [ 1899-02-1 ]
  • [ 58-61-7 ]
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  • [ 2140-79-6 ]
  • [ 1867-73-8 ]
  • [ 10300-22-8 ]
  • 17
  • [ 1899-02-1 ]
  • [ 58-61-7 ]
  • [ 57817-83-1 ]
  • [ 2140-79-6 ]
  • [ 1867-73-8 ]
  • [ 10300-22-8 ]
  • 18
  • [ 74230-06-1 ]
  • [ 58-61-7 ]
  • [ 57817-83-1 ]
  • [ 2140-79-6 ]
  • [ 15763-06-1 ]
  • [ 1867-73-8 ]
  • 19
  • [ 74230-06-1 ]
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  • [ 57817-83-1 ]
  • [ 2140-79-6 ]
  • [ 1867-73-8 ]
  • 20
  • [ 74230-06-1 ]
  • [ 58-61-7 ]
  • [ 57817-83-1 ]
  • [ 20649-46-1 ]
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  • [ 1867-73-8 ]
  • 21
  • [ 74230-06-1 ]
  • [ 58-61-7 ]
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  • [ 57817-83-1 ]
  • [ 2140-79-6 ]
  • [ 10300-22-8 ]
  • 22
  • [ 58-61-7 ]
  • [ 74-88-4 ]
  • [ 2140-79-6 ]
  • [ 10300-22-8 ]
  • 23
  • [ 2140-79-6 ]
  • [ 1608-26-0 ]
  • 2'-O-methyl-trans-adenosine 3',5'-cyclic N,N-dimethylphosphoramidite [ No CAS ]
  • 24
  • [ 75-77-4 ]
  • [ 2140-79-6 ]
  • <i>O</i>3',<i>O</i>5'-bis-(<i>tert</i>-butyl-dimethyl-silanyl)-<i>O</i>2'-methyl-adenosine [ No CAS ]
  • 26
  • [ 2140-79-6 ]
  • [ 88091-70-7 ]
  • [ 185761-07-3 ]
  • 27
  • [ 58-61-7 ]
  • [ 18107-18-1 ]
  • [ 2140-79-6 ]
  • [ 10300-22-8 ]
  • 28
  • [ 2140-79-6 ]
  • Phosphoric acid mono-[(2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-4-methoxy-2-phosphonooxymethyl-tetrahydro-furan-3-yl] ester [ No CAS ]
  • 29
  • [ 2140-79-6 ]
  • [ 3881-21-8 ]
YieldReaction ConditionsOperation in experiment
With cis-nitrous acid; acetic acid; In water; Commercially available 2?OMe-adenosine compound 14 was diazotized in aqueous acetic acid with nitrous acid to give compound 15 (step i) by the method of Hyde, 2003, J Med Chem, 46:1878-85 (hereby incorporated by reference). Compound 15 was converted to a compound 16 by the method of Miller, 2015, J Med Chem, 58:6248-6263 (hereby incorporated by reference) (step ii). The m62?OMe-adenosine product (compound 16) was protected by the method of Zhu, 2003, Synthetic Communications, 33:1233-43 (hereby incorporated by reference) (step iii). The adenosine compound was reacted with 1.1 equivalents of TMSCl per hydroxy group together with 1.2 equivalents of benzoyl chloride to produce TMS-modified, mono-benzoylated m62?OMe-adenosine. The TMSA groups were removed under aqueous acidic conditions in THF-TFA to give compound 17 (step iii). The 5?-hydroxy was reacted with DMT-Cl to form an ether and the phosphorylated adenosine compound 18 was produced as in Example 2 by reaction with 4-chlorophenyl dichlorophosphate as a 3?-O-phosphorylating agent (FIG. 7, step iv) to produce benzoyl-3?-p-m62?-OMeA (compound 18).
  • 31
  • [ 2140-79-6 ]
  • [ 66224-66-6 ]
  • Phosphoric acid mono-((2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl) ester [ No CAS ]
  • 32
  • [ 76-83-5 ]
  • [ 2140-79-6 ]
  • [ 28990-73-0 ]
  • 33
  • [ 2140-79-6 ]
  • [ 18162-48-6 ]
  • [ 251296-61-4 ]
YieldReaction ConditionsOperation in experiment
83% With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20℃; for 28h; DMAP (20 mg, 0.18 mmol) and imidazole (580 mg, 8.54 mmol) were added to a solution of <strong>[2140-79-6]2'-O-methyladenosine</strong> (1) (200 mg, 0.71 mmol) in DMF (5.5 mL), followed by the addition of TBSCl (640 mg, 0.43 mmol) and stirred at room temperature. After 28 h, the reaction mixture was quenched with water and extracted with AcOEt. The organic layer was dried over Na2SO4, and evaporated to give a colorless oil. The crude oil was purified by column chromatography (Kanto 60 N, Hexane/AcOEt = 1:1) to give a white foam (300 mg, 0.589 mmol, 83%). (IR (cm-1): 2929, 2857, 1672, 1599, 1472. 1H NMR (400 MHz, CDCl3) delta (ppm): 8.32 (1H, s), 8.25 (1H, s), 6.30 (2H, br), 6.13 (1H, d, J = 3.7 Hz), 4.50 (1H, dd, J = 4.6, 5.2 Hz), 4.12-4.11 (H, m), 4.01-3.98 (1H, m), 3.79-3.76 (1H, m), 3.47 (3H, s), 0.92 (9H, s), 0.91 (9H, s), 0.10 (6H, s), 0.09 (6H, s). ESI-MS (M+H)+: 510.29.) A solution of this white foam (300 mg, 0.59 mmol) in CH2Cl2 (5.7 mL) was cooled to 0 C in an ice bath. TMSCl (145 muL) was dropwise added to the reaction mixture, and then tert-butylnitrite (350 muL) was dropwise added at 0 C. After stirring for 7 h at 0 C, the reaction mixture was quenched with a saturated NaHCO3 solution, and extracted with CH2Cl2. The organic layer was dried over Na2SO4, and evaporated to give a colorless oil. The oil was purified by column chromatography (Kanto 60 N, Hexane/AcOEt = 5:1) to give 2 as a colorless oil (115 mg, 0.22, 37%) and recovery of the starting material (57 mg, 0.11 mmol, 19%). IR (cm-1): 2929, 2857, 1587, 1559, 1472, 1333, 1126. 1H NMR (400 MHz, CDCl3) delta (ppm): 8.73 (1H, s), 8.51 (1H, s), 6.20 (2H, d, J = 4.0 Hz), 4.50 (1H, t, J = 4.9 Hz), 4.15-4.11 (2H, m), 3.99 (1H, dd, J = 3.1, 11 Hz), 3.78 (1H, dd, J = 2.4, 11 Hz), 3.47 (3H, s), 0.92 (9H, s), 0.91 (9H, s), 0.10 (6H, s), 0.09 (6H, s). 13C NMR (125 MHz, CDCl3) delta (ppm): 152.0, 151.2, 151.1, 143.9, 132.3, 87.0, 85.5, 84.1, 69.7, 61.9, 58.5, 26.0, 25.7, 18.5, 18.1, -4.7, -4.8, -5.3, -5.4. HRESI-MS m/z: calcd for (M+H)+ C23H42N4O4Si2Cl, 529.2428; found, 529.2476..
With pyridine; 1H-imidazole; at 20℃; for 15h; To a solution of 7-1 (15.0 g, 53.3 mmol) in dry pyridine (150 mL) was added TBSC1 (20.0 g, 133.3 mmol) and Imidazole (10.8 g, 159.9 mmol). The mixture was stirred at r.t. for l5h. TLC showed 7-1 was consumed completely. The reaction mixture was concentrated in vacuo to give residue. The residue was quenched with DCM (500 mL). The DCM layer was washed with H2O (1 L*2) 2 times and brine. The DCM layer concentrated in vacuo to give crude 7-2 (27.2 g, 53.3 mmol) as a yellow oil. The crude 7-2 was used in next step directly. ESI-LCMS m/z 510.5 [M+H]+.
YieldReaction ConditionsOperation in experiment
0.25 g (80%) 2'-O-Methyl Adenosine (8) Solution of compound 7 (0.45 g, 1.17 mmol) in saturated methanolic ammonia (20 mL) was autoclaved at 125 C. for 4 hours. The solvent was removed in vacuo and remaining residue was purified by flash chromatography on silica gel. Elution with methylene chloride--methanol (9:1) mixture provided 0.25 g (80%) of 2'-O-methyl adenosine 8 as white solid. The analytical sample was recrystallized from abs EtOH. m.p. The product was identical to authentic sample by HPLC, UV-, 1 H-NMR-spectroscopy.
  • 36
  • yeast-ribonucleic acid [ No CAS ]
  • [ 2140-79-6 ]
  • 37
  • [ 17287-03-5 ]
  • [ 58-61-7 ]
  • [ 60037-52-7 ]
  • [ 57817-83-1 ]
  • [ 20649-46-1 ]
  • [ 2140-79-6 ]
  • [ 1867-73-8 ]
  • [ 10300-22-8 ]
YieldReaction ConditionsOperation in experiment
With copper acetylacetonate In N,N-dimethyl-formamide at 70℃; for 1h;
  • 38
  • [ 194034-61-2 ]
  • [ 2140-79-6 ]
YieldReaction ConditionsOperation in experiment
80% Subsequent amination of (7) with methanolic ammonia at 125 C. for 4 hours yields 2'-O-Methyl-adenosine (8) in 80% yield.
  • 39
  • [ 17287-03-5 ]
  • [ 58-61-7 ]
  • [ 2140-79-6 ]
  • 40
  • [ 2140-79-6 ]
  • [ 268748-00-1 ]
  • 42
  • [ 2140-79-6 ]
  • [ 123-76-2 ]
  • [ 647834-88-6 ]
  • 43
  • [ 2140-79-6 ]
  • [ 647834-80-8 ]
  • 5'-O-levulinyl-2'-O-methyladenosine [ No CAS ]
  • 44
  • [ 2140-79-6 ]
  • [ 647834-80-8 ]
  • 3'-O-levulinyl-2'-O-methyladenosine [ No CAS ]
  • 5'-O-levulinyl-2'-O-methyladenosine [ No CAS ]
  • [ 647834-88-6 ]
  • 45
  • [ 2140-79-6 ]
  • [ 98-88-4 ]
  • [ 1000003-68-8 ]
YieldReaction ConditionsOperation in experiment
72% With pyridine; at 80℃; for 4h; Example 15; Preparation of (2R,3R,4R,5R)-5-(6-amino-2-methoxy-9H-purin-9-yl)-2-(hvdroxymethyl)-4-methoxytetrahvdrofuran-3-ol 14; Scheme 14; To a solution of 2'-methoxy adenosine (1Og, 35.6mmol) in pyridine (75mL) was added benzoyl chloride (22.7mL, 196mmol) and the resulting solution was refluxed at 8O0C for 4h. The solvents were removed in vacuo and the residue dissolved in EtOAc and washed with aq. NaHCO3, brine and water, and the organic phase dried over MgSO4. Crystallisation from ethanol afforded 25 as a white solid in 2 batches (13.7g and 4.3g, 72% overall).
72% To a solution of 2'-methoxy adenosine (10 g, 35.6 mmol) in pyridine (75 mL) was added benzoyl chloride (22.7 mL, 196 mmol) and the resulting solution was refluxed at 80 C. for 4 h. The solvents were removed in vacuo and the residue dissolved in EtOAc and washed with aq. NaHCO3, brine and water, and the organic phase dried over MgSO4. Crystallisation from ethanol afforded 26 as a white solid in 2 batches (13.7 g and 4.3 g, 72% overall).
  • 46
  • [ 2140-79-6 ]
  • C11H13N5O5 [ No CAS ]
  • 47
  • [ 2140-79-6 ]
  • [ 49617-83-6 ]
  • N6-(3-iodobenzyl)-2'-O-methyladenosine [ No CAS ]
  • 48
  • [ 2140-79-6 ]
  • [ 1053644-11-3 ]
  • 49
  • [ 2140-79-6 ]
  • [ 532930-98-6 ]
  • 50
  • [ 2140-79-6 ]
  • [ 532930-93-1 ]
  • 51
  • [ 2140-79-6 ]
  • [ 296802-63-6 ]
  • 52
  • [ 2140-79-6 ]
  • Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-4-methoxy-5-(6-oxo-1-propyl-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester [ No CAS ]
  • 53
  • [ 2140-79-6 ]
  • Acetic acid (2R,3R,4R,5R)-2-acetoxymethyl-4-methoxy-5-(1-propyl-6-thioxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester [ No CAS ]
  • 54
  • [ 2140-79-6 ]
  • [ 532930-95-3 ]
  • 55
  • [ 2140-79-6 ]
  • [ 532930-99-7 ]
  • 56
  • [ 2140-79-6 ]
  • [ 296802-64-7 ]
  • 57
  • [ 2140-79-6 ]
  • [ 532930-94-2 ]
  • 58
  • [ 2140-79-6 ]
  • [ 532931-00-3 ]
  • 59
  • [ 2140-79-6 ]
  • [ 532930-96-4 ]
  • 60
  • [ 2140-79-6 ]
  • [ 532930-97-5 ]
  • 61
  • [ 2140-79-6 ]
  • [ 296802-65-8 ]
  • 62
  • [ 2140-79-6 ]
  • 3'-O-levulinyl-2'-O-methyladenosine [ No CAS ]
  • 63
  • [ 2140-79-6 ]
  • 5'-O-levulinyl-2'-O-methyladenosine [ No CAS ]
  • 64
  • [ 2140-79-6 ]
  • [ 65798-52-9 ]
  • 65
  • [ 2140-79-6 ]
  • Phosphoric acid (2R,3R,4R,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-4-methoxy-tetrahydro-furan-2-ylmethyl ester methyl ester [ No CAS ]
  • 66
  • [ 2140-79-6 ]
  • Benzoic acid (2R,3R,4R,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(6-dibenzoylamino-purin-9-yl)-4-methoxy-tetrahydro-furan-3-yl ester [ No CAS ]
  • 67
  • [ 2140-79-6 ]
  • Benzoic acid (2R,3R,4R,5R)-2-[(2-cyano-ethoxy)-methoxy-phosphanyloxymethyl]-5-(6-dibenzoylamino-purin-9-yl)-4-methoxy-tetrahydro-furan-3-yl ester [ No CAS ]
  • 68
  • [ 2140-79-6 ]
  • [ 312710-17-1 ]
  • 71
  • [ 2140-79-6 ]
  • 2'-O-(tert-butyldimethylsilyl)-3'-(N-carbonylmethyl)-3'-deoxy-5'-O-(dimethoxytrityl)-5-methyluridinyl-(3'-5')-5'-amino-5'-deoxy-2'-O-methyl-5-methyladenosine [ No CAS ]
  • 72
  • [ 2140-79-6 ]
  • 2'-O-(tert-butyldimethylsilyl)-3'-(N-carbonylmethyl)-3'-deoxy-5'-O-(dimethoxytrityl)-adenosinyl-(3'-5')-5'-amino-5'-deoxy-2'-O-methyl-5-methyladenosine [ No CAS ]
  • 73
  • [ 2140-79-6 ]
  • Pent-4-enoic acid (9-{(2R,3R,4R,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-methoxy-tetrahydro-furan-2-yl}-9H-purin-6-yl)-amide [ No CAS ]
  • 74
  • [ 2140-79-6 ]
  • Pent-4-enoic acid [9-((2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-methoxy-tetrahydro-furan-2-yl)-9H-purin-6-yl]-amide [ No CAS ]
  • 75
  • [ 2140-79-6 ]
  • Pent-4-enoic acid [9-((2R,3R,4R,5R)-3-methoxy-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-amide [ No CAS ]
  • 77
  • [ 2004-07-1 ]
  • [ 2140-79-6 ]
  • 78
  • [ 194034-59-8 ]
  • [ 2140-79-6 ]
  • 79
  • [ 244184-56-3 ]
  • [ 2140-79-6 ]
  • 81
  • [ 2140-79-6 ]
  • (2R,4S,5R)-5-(6-Amino-purin-9-yl)-4-methoxy-2-trityloxymethyl-dihydro-furan-3-one [ No CAS ]
  • 84
  • [ 2140-79-6 ]
  • 9-[4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-3-methoxy-5-trityloxymethyl-tetrahydro-furan-2-yl]-9<i>H</i>-purin-6-ylamine [ No CAS ]
  • 86
  • [ 2140-79-6 ]
  • N6-benzoyl-9-[methyl 6,10-anhydro-3,8,9-tri-O-(tert-butyldimethylsilyl)-2-O-methyl-β-D-arabino-L-ido-7-undeculofuranuronyl]adenine [ No CAS ]
  • 87
  • [ 2140-79-6 ]
  • N6-benzoyl-9-[methyl 6,10-anhydro-3,8,9-tri-O-(tert-butyldimethylsilyl)-2-O-methyl-α-D-arabino-L-ido-7-undeculofuranuronyl]adenine [ No CAS ]
  • 88
  • [ 2140-79-6 ]
  • 3-[5-(6-benzoylamino-purin-9-yl)-3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-4-methoxy-tetrahydro-furan-2-yl]-hydroxy-methyl}-6,6,8,8-tetraisopropyl-4-oxo-tetrahydro-2,5,7,9-tetraoxa-6,8-disila-benzocycloheptene-1-carboxylic acid methyl ester [ No CAS ]
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