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[ CAS No. 69655-05-6 ] {[proInfo.proName]}

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Chemical Structure| 69655-05-6
Chemical Structure| 69655-05-6
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Product Details of [ 69655-05-6 ]

CAS No. :69655-05-6 MDL No. :MFCD00077728
Formula : C10H12N4O3 Boiling Point : -
Linear Structure Formula :- InChI Key :BXZVVICBKDXVGW-NKWVEPMBSA-N
M.W : 236.23 Pubchem ID :135398739
Synonyms :
Didanosine;ddI;Videx EC;Videx;DIDEOXYINOSINE;69655-05-6;NSC 612049;2′,3′-Dideoxyinosine;ddl

Calculated chemistry of [ 69655-05-6 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 57.97
TPSA : 93.29 Ų

Pharmacokinetics

GI absorption : High
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) : -8.62 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : -1.24
Log Po/w (WLOGP) : -0.12
Log Po/w (MLOGP) : -0.75
Log Po/w (SILICOS-IT) : -0.34
Consensus Log Po/w : -0.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.78
Solubility : 38.9 mg/ml ; 0.165 mol/l
Class : Very soluble
Log S (Ali) : -0.22
Solubility : 141.0 mg/ml ; 0.598 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.99
Solubility : 24.1 mg/ml ; 0.102 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.28

Safety of [ 69655-05-6 ]

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 [ 69655-05-6 ]

* 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 [ 69655-05-6 ]

[ 69655-05-6 ] Synthesis Path-Downstream   1~83

  • 1
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  • [ 131933-66-9 ]
  • [ 131933-73-8 ]
  • 4
  • [ 69655-05-6 ]
  • [ 254887-64-4 ]
  • C13H17N4O6PS [ No CAS ]
  • 6
  • [ 69655-05-6 ]
  • [ 623-66-5 ]
  • [ 142894-15-3 ]
  • 7
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  • [ 638-08-4 ]
  • [ 142894-16-4 ]
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  • [ 93-97-0 ]
  • [ 117312-02-4 ]
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  • [ 389128-06-7 ]
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  • [ 141684-85-7 ]
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  • [ 68-94-0 ]
  • [ 5983-09-5 ]
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  • 13
  • [ 4097-22-7 ]
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YieldReaction ConditionsOperation in experiment
immobilized rec human adenosine deaminase enzyme; In water; at 20 - 40℃; for 1.5 - 120h;pH 6.5 - 7.5; 100.0 g ddA is added to 1900 ml of water at 30 C. (mother liquor from previous runs can also be used). After the ddA has been added (complete dissolution is not necessary), 4000 U of immobilized rec human adenosine deaminase is added. The reaction is maintained at 30 C. while stirring. The reaction is complete (approximately 5-8 hours) when the level of residual ddA is less than or equal to 1% of the original amount of ddA added. The enzyme solids are removed by filtration (20-30 mum media) and the enzyme cake is washed with 100 ml water. The used enzyme is held as a wet cake at 0-5 C. (for up to 72 hours) and can be recycled to another batch. The ddI solution is filtered through a CUNO filtration pad (0.4 to 1 micron), then through 0.2 micron filter media. A column (h/d ratio=6) is slurry packed with 380 U of immobilized rec human adenosine deaminase with water. The column is washed with 30 mM of NH4OH to pH 9.5 then with water to pH 6.5-7.5. While maintaining the temperature at 20 C., a 4% solution of ddA in water is passed through the column at a rate of 7.2 mil/min. for 120 hours. The effluent from the column is at pH 9.2-9.5 and contains >99% ddI with <1% ddA remaining. The resulting ddI solution is filtered through a CUNO pad and a 0.21mu filter before final isolation. A column (h/d ratio=2.7) is slurry packed with 1000 U of immobilized rec human adenosine deaminase with water. 25.0 g of ddA is dissolved in 475 ml of water (or a mother liquor from previous batch, diluted with water to 475 ml) at 30 C. in a 3-neck round bottom flask equipped with a mechanical stirrer. The ddA solution is circulated at 30 C. through the enzyme column at -50 mL/min (circulation speed can be varied as necessary). [0093] The reaction is complete (approximately 3-9.5 hours) when the level of residual ddA is less than or equal to 1% of the original amount of ddA added by HPLC analysis. The column is then rinsed with 25 ml of water and can be held at 0-5 C. (for up to 72 hours) for reuse. The resulting ddI solution is filtered through a CUNO pad and a 0.2 mum filter before final isolation. The following Table describes the conversion of a 52-60 g/L solution of ddA in water to ddI using the microbial adenosine deaminase as described above versus an example using the recombinant human ADA immobilized enzyme following the general procedure in Example 4. As can be seen from the results of Table 2, the recombinant human immobilized enzyme is significantly more stable than microbial enzymes and allows for the completion of the reaction with less units of enzyme and in a short period of time.
microbial adenosine deaminase enzyme; In water; at 37 - 40℃; for 16 - 24h; Microbial ADA from recombinant E. coli was partially purified and isolated as an ammonium sulfate suspension. E. coli fermentation broth (42 U ADA/mL, 2 L) was centrifuged and the cell pellet was collected and washed with 1 L 100 mM phosphate buffer pH 7.5. The cells were again centrifuged and resuspended in 2 L of the above buffer plus 20% glycerol. The cells were passed once through a microfluidizer. Cell debris was removed by centrifugation and the resulting supernatant was concentrated by ultrafiltration through a 30,000 MWCO cassette. The enzyme was concentrated to a final titer of 390 U/ml. Ammonium sulfate was added to a 50% saturation, the resulting precipitate was collected by centrifugation and re-suspended in 100 ml deionized water. The final titer of the slurry was 740 U/ml; the protein content of the slurry was 75 mg/ml. [0098] The following Table describes the conversion of a 52-60 g/L solution of ddA in water to ddI using the microbial adenosine deaminase as described above versus an example using the recombinant human ADA immobilized enzyme following the general procedure in Example 4. As can be seen from the results of Table 2, the recombinant human immobilized enzyme is significantly more stable than microbial enzymes and allows for the completion of the reaction with less units of enzyme and in a short period of time.
Enzymatic reaction; After 368 g of a mixed solution of acetonitrile and water containing 19.4 wt% of 9-(2,5-O-diacetyl-3-bromo-3-deoxy-beta-D-xylofuranosyl)adenine (71.3 g, 172 mmol) was poured into a 500-ml eggplant-shaped flask, the solution was adjusted to the pH range of 8.5 to 10.5 by the addition of aqueous sodium hydroxide solution. Thereafter, 1.65 g of the fresh catalyst (B) (0.0046 equivalent on a basis of palladium atom) and 26.6 g of the wet catalyst (B) obtained just after collected without the drying process were added and hydrogen was blown into the reaction system to carry out a reduction reaction, with the reaction system being maintained under basic condition by use of aqueous sodium hydroxide solution. The reduction reaction was completed in 3.8 hours. After completion of the reduction, the reaction liquid was subjected to filtration to collect 33.4 g of the catalyst. It took 0.5 hours to take out the catalyst by filtration. Apart of the filtrate was subjected to saponification by the addition of aqueous sodium hydroxide solution. According to the quantitative analysis by HPLC, 2',3'-dideoxyadenosine was found to be obtained in a yield of 83%. The remaining filtrate was concentrated and subjected to saponification by the addition of aqueous sodium hydroxide solution. Through the steps of extraction and crystallization, 29.4 g of 2',3'-dideoxyadenosine was obtained in a yield of 66% as wet crystals (not dried). Furthermore, the obtained crystals were subjected to enzymatic deamination, whereby 2',3'-dideoxyinosine was obtained.
  • 14
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  • [ 171284-20-1 ]
  • (Rp)- and (Sp)-4-acetyloxybenzyl (3'-azido-3'-deoxythymidin-5-yl) (2',3'-dideoxyinosin-5'-yl) phosphate [ No CAS ]
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  • [ 30516-87-1 ]
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  • [ 171284-22-3 ]
  • (Rp)- and (Sp)-4-pivaloyloxybenzyl (3'-azido-3'-deoxythymidin-5-yl) (2',3'-dideoxyinosin-5'-yl) phosphate [ No CAS ]
  • 16
  • [ 30516-87-1 ]
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  • [ 171284-21-2 ]
  • (Rp)- and (Sp)-4-butanoyloxybenzyl (3'-azido-3'-deoxythymidin-5-yl) (2',3'-dideoxyinosin-5'-yl) phosphate [ No CAS ]
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  • [ 125790-82-1 ]
  • [ 13146-72-0 ]
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  • 8-Bromo-9-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-1,9-dihydro-purin-6-one [ No CAS ]
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  • [ 18162-48-6 ]
  • [ 177779-56-5 ]
  • 20
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  • [ 1609-47-8 ]
  • 2',3'-dideoxyinosine-5'-yl-O-ethyl carbonate [ No CAS ]
  • 21
  • [ 177779-55-4 ]
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  • 22
  • [ 69655-05-6 ]
  • 1,2-dihexadecyl-sn-glycero-3-H-phosphonate triethylammonium salt [ No CAS ]
  • C45H83N4O7P [ No CAS ]
  • 23
  • [ 69655-05-6 ]
  • [ 203568-78-9 ]
  • 11-{4-[(2S,5R)-5-(6-Oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethoxycarbonyl]-butyl}-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester [ No CAS ]
  • 24
  • [ 69655-05-6 ]
  • [ 208449-63-2 ]
  • 11-{4-[(2S,5R)-5-(6-Oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethoxycarbonyl]-butyryl}-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester [ No CAS ]
  • 25
  • [ 205189-72-6 ]
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  • 26
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  • [ 192752-93-5 ]
  • 9-[(2R,5S)-5-(8-Methyl-4H-benzo[1,3,2]dioxaphosphinin-2-yloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one [ No CAS ]
  • 27
  • [ 177779-56-5 ]
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YieldReaction ConditionsOperation in experiment
In water; at 0 - 40℃; for 1h;pH 7.8 - 8.3;Purification / work up; The ddI solution is distilled under vacuum at an internal batch temperature of 20-40 C. The distillation is stopped when the concentration of ddI reaches 10-12% w/v based on initial ddA. Typically the pH is 8.1-8.3 at this point. Additional water is added and distillation is then continued until the concentration again reaches 10-12%, and the pH of the ddI slurry is less than 8 (typically 7.8-7.9). The ddI suspension is cooled to 0-5 C. and held for at least 1 hour. The cold slurry is filtered and the cake is washed with 0-5 C. water. The mother liquor and aqueous wash can be retained for recycling in another batch. [0096] The cake is washed with 0-5 C. acetone. The solids are dried under vacuum at 45-50 C. to a constant weight. Yields of 82% for the first run and 96-99% for four subsequent runs (>96% overall) are expected with mother liquor recycling. The resulting ddI is >99% pure.
  • 29
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  • [ 246023-08-5 ]
  • 2',3'-dideoxyinosylyl-(5'->5')-N4-palmitoyl-2',3'-dideoxycytidine [ No CAS ]
  • 30
  • [ 108-55-4 ]
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  • Pentanedioic acid mono-[(2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester [ No CAS ]
  • 31
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  • [ 152336-79-3 ]
  • Pentanedioic acid (2S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester (2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]
  • 32
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  • [ 128305-54-4 ]
  • Pentanedioic acid (2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]
  • 33
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  • Pentanedioic acid mono-[(2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester [ No CAS ]
  • Pentanedioic acid bis-[(2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester [ No CAS ]
  • 34
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  • [ 61447-32-3 ]
  • C13H19N4O4PS [ No CAS ]
  • 35
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  • [ 676329-52-5 ]
  • C16H23N4O4PS [ No CAS ]
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  • [ 676329-49-0 ]
  • C26H45N4O4PS [ No CAS ]
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  • [ 110143-10-7 ]
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  • [ 120503-34-6 ]
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  • [ 530-62-1 ]
  • C10H11N4O3(CONCHCHNCH) [ No CAS ]
  • 40
  • C50H95N2O8P [ No CAS ]
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  • C54H92N5O11P [ No CAS ]
  • 41
  • [ 90393-21-8 ]
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  • C50H84N4O10 [ No CAS ]
  • 42
  • 5'-O-benzyl-2',3'-dideoxyinosine [ No CAS ]
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  • 43
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  • C10H11N4O3(COSCH2CH2NHCOOC4H9) [ No CAS ]
  • 44
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  • C10H11N4O3(COSCH2CH2NH2) [ No CAS ]
  • 45
  • [ 69655-05-6 ]
  • C10H11N4O3(COSCH2CH2NHCO)C10H12N5O4 [ No CAS ]
  • 46
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  • C10H11N4O3(COSCH2CH2NHCO)C10H12N5O4 [ No CAS ]
  • 47
  • [ 69655-05-6 ]
  • C10H11N4O3(COSCH2CH2NHCO)C10H11N2O4 [ No CAS ]
  • 48
  • [ 69655-05-6 ]
  • Pentanedioic acid bis-[(2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester [ No CAS ]
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  • 1-(2-deoxy-α,β-D-erythro-pentofuranosyl)imidazo[4,5-d]pyridazine-4(5H)-one [ No CAS ]
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  • 51
  • imidazole-1-carbothioic acid <i>O</i>-[2-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester [ No CAS ]
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  • [ 260562-60-5 ]
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  • 54
  • [ 205189-74-8 ]
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  • 55
  • Methanesulfonic acid (2R,3R,4R,5R)-5-formyloxymethyl-4-methanesulfonyloxy-2-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl ester [ No CAS ]
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  • 56
  • [ 69655-05-6 ]
  • Phosphoric acid (R)-2,3-bis-hexadecyloxy-propyl ester (2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]
  • 57
  • [ 69655-05-6 ]
  • Thiophosphoric acid O-((R)-2,3-bis-hexadecyloxy-propyl) ester O'-[(2S,5R)-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl] ester [ No CAS ]
  • 58
  • [ 890-38-0 ]
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  • 59
  • [ 69655-05-6 ]
  • Acetic acid (2S,5R)-5-(8-bromo-6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-2-ylmethyl ester [ No CAS ]
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  • [ 93778-57-5 ]
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  • [ 177779-54-3 ]
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  • [ 32780-06-6 ]
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  • 63
  • (3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-phenylselanyl-tetrahydro-furan-2-ol [ No CAS ]
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  • [ 149656-26-8 ]
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  • [ 102717-29-3 ]
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  • [ 32780-07-7 ]
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  • [ 505-54-4 ]
  • [ 69655-05-6 ]
  • [ 879015-25-5 ]
YieldReaction ConditionsOperation in experiment
50.5% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; A mixture of didanosine (300 mg), hexadecanedioic acid (1.26 g), dimethylaminopyridine (80 mg), N- (3- DIMETHYLAMINOPROPYL)-N -ETHYL-CARBODIIMIDE hydrochloride (300 mg) in THF (50 ml) was stirred overnight at ambient temperature. The mixture was evaporated and the title compound was isolated by flash chromatography (silica, methanol: CH2CL2=2 : 8) plus 2% NH3 solution (25%) as a white powder. Yield: 323 mg (50. 5%) NMR (DMSO-D6) : 1. 22-2. 50 (m), 4.14-4. 25 (m), 6. 24 (t), 8.07 (s), 8.24 (s). ) MS: 505 (M+H)
50.5% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 20℃; A mixture of didanosine (300 mg) , hexadecanedioic acid (1.26 g) , dimethylaminopyridine (80 mg) , N- (3- dimethylaminopropyl) -N'-ethyl-carbodiimide hydrochloride (300 mg) in THF (50 ml) was stirred overnight at ambient temperature. The mixture was evaporated and the title compound was isolated by flash chromatography (silica, methanol:CH2Cl2=2:8) plus 2% NH3 solution (25%) as a white powder. Yield: 323 rag (50.5%)NMR (DMSO-d*) : 1.22 - 2.50 (m) , 4.14 - 4.25 (m) , 6.24 (t) , 8.07 (s) , 8.24 (s) .MS: 505 (M+H)
  • 80
  • [ 100-21-0 ]
  • [ 69655-05-6 ]
  • [ 879015-30-2 ]
YieldReaction ConditionsOperation in experiment
12% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0℃; 2, 3'dideoxyinosine (100 mg, 0.424 mmol), 1,4- benzenedicarboxylic acid (281 mg, 1.69 MMOL), DMAP (20 mg, 1.64 mmol) and THF (12 ml) was stirred on an ice bath. N- (-3-DIMETHYLAMINOPROPYL)-N - ethylcarbodiimidehydrochloride (106 mg, 0.553 mmol) was added. The mixture was shaken and stirred overnight. Aqueous ammonia (1 ml), MEOH (10 ml) and DCM (10 ml) was added. The mixture was shaken, silica added, concentrated and purified by chromatography on silica using 30-40% MEOH, 5% aqueous ammonia in DCM
12% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0℃; 2, 3 'dideoxyinosine (100 mg, 0.424 mmol), 1,4- benzenedicarboxylic acid (281 mg, 1.69 mmol), DMAP (20 mg, 1.64 mmol) and THF (12 ml) was stirred on an ice bath. N- (-3-Dimethylaminopropyl) -N'- ethylcarbodiimidehydrochloride (106 mg, 0.553 mmol) was added. The mixture was shaken and stirred overnight. Aqueous ammonia (1 ml), MeOH (10 ml) and DCM (10 ml) was added. The mixture was shaken, silica added, concentrated and purified by chromatography on silica using 30-40% MeOH, 5% aqueous ammonia in DCM
  • 81
  • [ 24424-99-5 ]
  • [ 69655-05-6 ]
  • [ 879015-29-9 ]
YieldReaction ConditionsOperation in experiment
46% With 1,8-diazabicyclo[5.4.0]undec-7-ene;dmap; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; 2 , 3 -DIDEOXYINOSINE (1 g, 4.24 mmol), 1, 8-Diaza-7- bicyclo [5.4. 0] undecene (1.29 g, 8.47 mmol), 4- DIMETHYLAMINOPYRIDINE (small catalytic amount) and DMF (10 ml) was stirred on an ice bath. Bocanhydride (1.4 g, 8.04 mmol) dissolved in DMF (10 ml) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was concentrated, 20 ml DCM added and washed with 3X20 ml NAHCO3. The organic phase was dried with sodium sulphate, filtered, concentrated and purified by chromatography on silica using 12. 5% MEOH 2% aqueous ammonia in DCM. Resulting in 611 mg white crystalline product. 46% Yield.
2T , 3 '-dideoxyinosine (I g, 4.24 mmol) , l,8-Diaza-7- bicyclo[5.4.0]undecene (1.29 g, 8.47 mmol), 4- dimethylaminopyridine (small catalytic amount) and DMF (10 ml) was stirred on an ice bath. Bocanhydride (1.4 g, 8.04 mmol) dissolved in DMF (10 ml) was added. The reaction mixture was stirred at room temperature over night. The reaction mixture was concentrated, 20 ml DCM added and washed with 3x20 ml NaHCO3. The organic phase was dried with sodium sulphate, filtered, concentrated and purified by chromatography on silica using 12.5% MeOH 2% aqueous ammonia in DCM. Resulting in 611 mg white crystalline product.46% Yield.
  • 82
  • [ 810694-79-2 ]
  • [ 69655-05-6 ]
YieldReaction ConditionsOperation in experiment
70% With sodium hydroxide; hydrogen;palladium(II) hydroxide/carbon; In methanol; dichloromethane; N,N-dimethyl-formamide; at 20 - 100℃; under 760.051 Torr; for 24h; Example 4 Synthesis of 2',3'-dideoxyinosine (DDI) To a N,N-dimethylformamide solution (1 mL) of N1,5'-O-dibenzyl-2',3'-dideoxyinosine (52 mg, 0.125 mmol), an aqueous solution of sodium hydroxide (0.3 mL) at a concentration of 1mol/L was added, and the mixture was stirred at room temperature for 2 hours. To the obtained solution, 20% palladium hydroxide - carbon (10 mg) was added, and the mixture was stirred at room temperature for 2 hours in an atmosphere of hydrogen (1 atm) and thereafter stirred at 80C for 16 hours and at 100C for 6 hours. The palladium catalyst was removed from the obtained reaction mixture by filtration, and the resultant filtrate was concentrated under reduced pressure. After purification by chromatography (using 10 g of silica gel and a mixed solvent of dichloromethane and methanol (4:1) as an eluding solution), 21 mg of the intended product was obtained in a yield of 70% as a white solid. 1H-NMR (DMSO-d6): delta 2.00-2.07 (m, 2H), delta 2.31-2.53 (m, 2H), delta 3.52 (m, 1H), delta 3.62 (m, 1H), delta 4.11 (m, 1H), delta 4.96 (m, 1H), delta 6.21 (d-d, 1H, J=6.8, 3.3 Hz); delta 8.05 (s, 1H), delta 8.33 (s, 1H). 13C-NMR (DMSO-d6): delta 25.77, 32.49, 62.96, 82.40, 84.80, 124.64, 138.54, 145.97, 147.94, 156.98. ESIMS m/z: 237 (M+H).
YieldReaction ConditionsOperation in experiment
By following the procedure of part A and substituting 3'-deoxythymidine with the following: ... 2',3'-dideoxycytidine, 2',3'-dideoxyguanosine, 9-(2,3-dideoxy-beta-D-erythro-pentofuranosyl)2-aminopurine, 9-(2,3-dideoxy-beta-D-erythro-pentofuranosyl)2,6-diaminopurine, 9-(2,3-dideoxy-beta-D-erythro-pentofuranosyl)hypoxanthine, and 1-(2,3-dideoxy-beta-D-erythro-pentofuranosyl)5-trifluoromethyluracil;
Same Skeleton Products
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