Home Cart 0 Sign in  

[ CAS No. 2004-06-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 2004-06-0
Chemical Structure| 2004-06-0
Structure of 2004-06-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 2004-06-0 ]

Related Doc. of [ 2004-06-0 ]

Alternatived Products of [ 2004-06-0 ]
Product Citations

Product Citations

Zhou, Jujun ; Deng, Youchao ; Iyamu, Iredia D. , et al. DOI: PubMed ID:

Abstract: S-Adenosyl-L-methionine (SAM) analogs are adaptable tools for studying and therapeutically inhibiting SAM-dependent methyltransferases (MTases). Some MTases play significant roles in host-pathogen interactions, one of which is Clostridioides difficile-specific DNA adenine MTase (CamA). CamA is needed for efficient sporulation and alters persistence in the colon. To discover potent and selective CamA inhibitors, we explored modifications of the solvent-exposed edge of the SAM adenosine moiety. Starting from the two parental compounds (6e and 7), we designed an adenosine analog (11a) carrying a 3-phenylpropyl moiety at the adenine N6-amino group, and a 3-(cyclohexylmethyl guanidine)-Et moiety at the sulfur atom off the ribose ring. Compound 11a (IC50 = 0.15 μM) is 10x and 5x more potent against CamA than 6e and 7, resp. The structure of the CamA-DNA-inhibitor complex revealed that 11a adopts a U-shaped conformation, with the two branches folded toward each other, and the aliphatic and aromatic rings at the two ends interacting with one another. 11a occupies the entire hydrophobic surface (apparently unique to CamA) next to the adenosine binding site. Our work presents a hybrid knowledge-based and fragment-based approach to generating CamA inhibitors that would be chem. agents to examine the mechanism(s) of action and therapeutic potentials of CamA in C. difficile infection.

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; 39684-80-5 ; ;

Product Details of [ 2004-06-0 ]

CAS No. :2004-06-0 MDL No. :MFCD26142246
Formula : C10H11ClN4O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 286.67 Pubchem ID :-
Synonyms :
6-Chloropurine riboside

Calculated chemistry of [ 2004-06-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 7.0
Num. H-bond donors : 3.0
Molar Refractivity : 63.28
TPSA : 113.52 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) : -7.86 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : 0.26
Log Po/w (WLOGP) : -1.23
Log Po/w (MLOGP) : -2.06
Log Po/w (SILICOS-IT) : -1.01
Consensus Log Po/w : -0.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.0
Solubility : 2.87 mg/ml ; 0.01 mol/l
Class : Very soluble
Log S (Ali) : -2.2
Solubility : 1.79 mg/ml ; 0.00624 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.56
Solubility : 79.0 mg/ml ; 0.275 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.71

Safety of [ 2004-06-0 ]

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 [ 2004-06-0 ]

* 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 [ 2004-06-0 ]
  • Downstream synthetic route of [ 2004-06-0 ]

[ 2004-06-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 2004-06-0 ]
  • [ 67-64-1 ]
  • [ 39824-26-5 ]
YieldReaction ConditionsOperation in experiment
87% With toluene-4-sulfonic acid In water ((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4- d][l,3]dioxol-4-yl)methanol-Toluenesulfonic acid monohydrate (19.8 g, 104 mmol) was added to a stirred suspension of (2R,3R,4S,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran- 3,4-diol (3.0 g, 10.5 mmol) in dried acetone (300 mL). The solid dissolved 15 min later. 2 h later, the solution was poured into stirred aqueous NaHC03 (0.5 N, 300 mL) slowly. After removed acetone in vacuo, the mixture was extracted with DCM (100 mL x 5). The combined organic layers were washed with water (100 mL) and brine (100 mL), then dried over Na2S04, filtered and concentrated to afford the target (3.0 g, yield: 87percent, purity >96percent) as a pale solid. 1H NMR (500 MHz, CD3OD) δ 8.71 (d, J = 1.0 Hz, 1H), 8.65 (d, J = 1.5 Hz, 1H), 6.23 (d, J = 2.0 Hz, 1H), 5.29 (dd, J = 2.0, 6.0 Hz, 1H), 4.96 (dd, J = 2.0, 6.0 Hz, 1H), 4.31 (d, J = 2.0 Hz, 1H), 3.68-3.59 (m, 2H), 1.51 (s, 3H), 1.29 (s, 3H) ppm; LCMS (m/z): 327.1 [M+l]+.
86%
Stage #1: With toluene-4-sulfonic acid In water at 25℃; for 6 h;
Stage #2: With sodium hydrogencarbonate In water
Compound 356l-(4-(tert-butyl)phenyl)-3-(3-((((2R,3S,4R,5R)-5-(6-(dimethylamino)-9H-purin-9-yl)-3,4- dihydroxytetrahydrofuran-2-yI)methyl)(isopropyl)amino)propyl)ureaStep 1. Preparation of ((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4-yl)methanolp-Toluenesulfonic acid monohydrate (134 g, 700 mmol) was added to a stirred suspension of (2R,3R,4S,5R)-2-(6-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran- 3,4-diol (20 g, 70 mmol) in acetone (100 mL). After stirred at 25° C for 6 h, the reaction mixture was poured into stirred aqueous NaHC03 (0.5 N, 2000 mL) slowly. After removed acetone in vacuo, the mixture was extracted with DCM (800 mL x 3). The combined organic layers were washed with water (500 mL) and brine (500 mL), then dried over Na2S04 and concentrated to afford the title compound (19.5 g, yield: 86 percent) as a white solid. NMR(500 MHz, CDC13): δ 8.75 (s, 1H), 8.30 (s, 1H), 6.01 (d, J = 4.5 Hz, 1H), 5.19-5.17 (m, 1H), 5.10-5.09 (m, 1H), 4.54 (s, 1H), 3.96 (dd, J = 1.0, 12.5 Hz, 1H), 3.82 (dd, J = 2.0, 12.5 Hz, 1H), 1.64 (s, 3H), 1.37 (s, 3H) ppm; ESI (m/z): 327.1 [M+l]+.
74.1% at 20℃; for 3 h; 200 mg (0.7 mmol) of the commercial precursor 6-chloropurine riboside and acetone (10 mL)were mixed under agitation at room temperature for 30 min. This was followed by the slowaddition of p-toluensulfonic acid (5.57 mmol). The solution was kept under stirring conditionsat room temperature for 3 h. The progress of the reaction was monitored by TLC. Sodiumbicarbonate (1.5 g) was added and maintained under agitation. Once the reaction was finished,the solid phase was removed and washed with ethyl acetate (2). The product was thenpurified by column chromatography with mixtures of CH2Cl2-MeOH, obtaining the compound[6-(6-Chloro-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-methanol (A); Yellow solid,74.1percent yield; m.p. 155–158 °C 1H–NMR (CDCl3, 400.1 MHz) δ 8.72 (s, 1H, CH-Ar purine); 8.31 (s, 1H,CH-Ar purine); 6.01 (d, J = 8.0 Hz, 1H, CH-1'); 5.16 (m, 1H, CH-2'); 4.97 (d, J = 7.83 Hz, 1H, CH-3');4.52 (d, J = 1.22 Hz, 1H, CH-4'); 3.83 (m, 2H, CH2-5'); 5.06 (m, 1 OH); 1.62 (s, 3H, ketal); 1.35 (s, 3H,ketal). 13C–NMR (CDCl3, 100.6 MHz) δ 151.6, 151.4, 148.8, 144.4, 132.5, 114.0, 93.4, 86.2, 83.2, 81.1,62.7, 27.1, 24.8. IR (KBr) λ/cm1 3320, 2906, 2863, 959, 733. Anal. Cal. C13H15ClN4O4: C = 47.75percent,H = 4.59percent, Cl = 10.85percent, N = 17.14percent.
Reference: [1] Nucleosides and Nucleotides, 1996, vol. 15, # 1-3, p. 619 - 629
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 7, p. 3848 - 3865
[3] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 8, p. 577 - 582
[4] Patent: WO2012/82436, 2012, A2, . Location in patent: Page/Page column 192-193
[5] Patent: WO2012/82436, 2012, A2, . Location in patent: Page/Page column 256-257
[6] Molecules, 2018, vol. 23, # 5,
[7] Journal of the American Chemical Society, 1961, vol. 83, p. 150,154
[8] Journal of the American Chemical Society, 1996, vol. 118, # 24, p. 5532 - 5543
[9] Journal of the American Chemical Society, 1996, vol. 118, # 29, p. 6880 - 6889
[10] Patent: WO2005/84653, 2005, A2, . Location in patent: Page/Page column 48
[11] Pr.IV.Congr.Biochem.Wien 1958,Bd.15,S.40,
[12] Organic Letters, 2015, vol. 17, # 6, p. 1513 - 1516
[13] Patent: WO2005/84653, 2005, A2, . Location in patent: Page/Page column 48
  • 2
  • [ 2004-06-0 ]
  • [ 77-76-9 ]
  • [ 39824-26-5 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With toluene-4-sulfonic acid In acetone at 20℃; for 16 h;
Stage #2: With water; sodium hydrogencarbonate In acetone
Example 1: ((2R/3S/4R/5R)-5-{6-[(lS)-2/3-dihydro-lH-inden-l-ylamino]9H-purin-9-yl}- 3,4-dmydroxytetrahydrofuran-2-yl)methyl sulfamate (1-2)Step a: [('3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2>2-dimethyltetrahydrofuro- r3,4-diri,31dioxol-4-yllmethanol; [0162] 6-Chloro-β-D-ribofuranosylpurine (8.17g, 28.5mmol), p-toluenesulfonic acid monohydrate (5.42g, 28.5mmol) and 2,2~dimethoxypropane(17.5mL, 142.5mmol) were mixed in acetone(500mL). The reaction mixture was stirred at room temperature for lβhours. Saturated aqueous NaHCO3 solution (40OmL) was then added and the mixture was evaporated under reduced pressure to remove most of the acetone. The remaining aqueous residue was then extracted with chloroform(4 x 20OmL). The combined organics were dried- 78 - EPO <DP n="79"/>over Na2SO4, and then evaporated to yield the product as a white amorphous solid (9.22g, 99percent).[0163] LCMS: R.t. 1.22 min ES+ 327 (formic acid).
97% With toluene-4-sulfonic acid In acetone at 20℃; To a stirred solution of chloropurine 23 (15.0 g, 52.2 mmol) in 175 mL of acetone was 2,2-dimethoxypropane (63.0mL, 538 mmol) followed by p-toluenesulfonic acid (10.9 g, 60 mmol). The resulting heterogeneous mixture wasstirred for 2.5 h at rt during which time the solution become homogenous and bright yellow. The volatiles were removed in vacuo to give a thick yellow oil. The oil was dissolved in 150 mL of EtOAc followed by the addition of 150 mL of saturated NaHCO3 over a period of 5 minutes during which time the yellow color disappeared. The resulting layers were separated and the aqueous layer was extracted with 2 × 150 mL of EtOAc. The combined organic layers were washed with 200 mL of brine, dried (Na2SO4) and concentrated in vacuo to give the acetonide S12
97% With toluene-4-sulfonic acid In acetone at 20℃; for 2 h; Next, electrophilic AMP analogs with two significantly different substituents at N6-position (i.e. a propargyl and phenyl alkyne) were synthesized following Scheme 2 and Scheme 3. Compound 2 that has a small hydrophobic group (propargyl alkyne) at the N6-position was prepared by coupling 2-chloroethanesulfonyl chloride with the 5-amino adenine moiety, followed by the deprotection of the acid labile acetonide (Scheme 2). The synthesis of compound 3, which has a large hydrophobic group (phenyl alkyne) at the N6-position, required tert-butyldimethylsilane (TI3DMS) protection and deprotection steps on the 5’ alcohol and Hoc protection on the N6-amine due to the instability of the reaction intermediates during the Mitsunobu reaction. Subsequent treatment with 2-chloroethanesulfonyl chloride and global deprotection of the acid labile protecting groups led to the formation of compound 3.
89.03% With toluene-4-sulfonic acid In acetone at 20℃; for 4 h; Inert atmosphere (2R, 5R) -2- (6- chloro -9H- purin-9-yl) -5- (hydroxymethyl) tetrahydrofuran-3,4-diol (4.8 g, 16.74 mmol) and 2,2 - dimethoxy-propane (10.26 mL, 83.71 mmol) toIn a nitrogen stream, and then p- toluene sulfonic acid monohydrate (3.18 g, 16.74 mmol) was dissolved in anhydrous acetone (120 mL) to It was added dropwise then stirred at room temperature for 4 hours.The completion of the reactionA check after the reaction with saturated aqueous sodium hydrogen carbonate solutionIt concludes.The reaction solutionThe organic layer was concentrated under reduced pressure with chloroform (4 X 20 mL) Extracted and washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate.Intermediate compound by separating the resulting residue was then concentrated under reduced pressure, by column chromatography ((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d] [1,3]dioxol-4-yl)methanol (4.87 g, 89.03percent a)Obtained.
83% With toluene-4-sulfonic acid In acetone at 20℃; for 2 h; Step 1
(2R,3R,4S,5R)-2-(6-Chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (5.47 g, yield: 72percent) was obtained according to the process described in the known method (Journal of Organic Chemistry (J. Org. Chem.), 2002, vol. 67, pp. 6708-67963 using (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (10.9 g, 26.4 mmol) synthesized by the method described in the known method [Journal of Medicinal Chemistry (J. Med. Chem.), 2012, vol. 55, pp. 1478-1489].
(2R,3R,4S,5R)-2-(6-Chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (5.48 g, 19.1 mmol) was suspended in acetone (200 mL), and 2,2-dimethoxypropane (11.7 mL, 95.5 mmol) and 4-toluenesulfonic acid monohydrate (9.09 g, 47.8 mmol) were added thereto, and the mixture was stirred at room temperature for 2 hours.
To the reaction solution was added a saturated aqueous sodium bicarbonate solution, and the solvent was evaporated under reduced pressure until the amount of the solvent was decreased to about half.
Chloroform was added thereto, and the mixture was extracted with chloroform and dried over sodium sulfate.
Then, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (heptane/ethyl acetate) to obtain ((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1.3]dioxol-4-yl)methanol (5.17 g, yield: 83percent).
ESI-MS (m/z): 327 (M+1)
83% With toluene-4-sulfonic acid In acetone at 20℃; for 2 h; (2R,3R,4S,5R)-2-(6-Chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (5.47 g, yield: 72percent) was obtained according to the process described in the known method [Journal of Organic Chemistry (J. Org. Chem.), 2002, vol. 67, pp. 6788-6796] using (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (10.9 g, 26.4 mmol) synthesized by the method described in the known method [Journal of Medicinal Chemistry (J. Med. Chem.), 2012, vol. 55, pp. 1478-1489].
(2R,3R,4S,5R)-2-(6-Chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol (5.48 g, 19.1 mmol) was suspended in acetone (200 mL), and 2,2-dimethoxypropane (11.7 mL, 95.5 mmol) and 4-toluenesulfonic acid monohydrate (9.09 g, 47.8 mmol) were added thereto, and the mixture was stirred at room temperature for 2 hours.
To the reaction solution was added a saturated aqueous sodium bicarbonate solution, and the solvent was evaporated under reduced pressure until the amount of the solvent was decreased to about half.
Chloroform was added thereto, and the mixture was extracted with chloroform and dried over sodium sulfate.
Then, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (heptane/ethyl acetate) to obtain ((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (5.17 g, yield: 83percent).
ESI-MS (m/z): 327 (M+1)
79%
Stage #1: With toluene-4-sulfonic acid In acetone at 20℃; for 45 h;
Stage #2: With sodium hydroxide In water for 0.0333333 h;
To a 200-L reactor with moderate stirring were charged acetone (115 L, 23 vol) and 6-chloropurine-9-riboside (5.0 kg, 17.4 mol, 1.0 wt/1.0 vol). Subsequently, p- TsOH"H2O (166 g, 0.88 mol, 0.05 equiv, 0.033 wt) and 2,2-dimethoxypropane (7.6 L, 62 mol, 3.54 equiv, 1.52 vol) were added and the resulting yellow suspension stirred at ambient temperature. After 45 h, a sample of the resulting yellow-green solution was taken and analysis by HPLC revealed the starting material to be present at 0.42percent by conversion (overall purity 96.9 area percent). The batch was neutralized by the addition of IN NaOH (900 rnL, 0.90 mol, 0.05 equiv, 0.18 vol). This addition took approximately 2 min; the final pH was pH 7. The batch was allowed to stir for 1 h. The resulting cloudy yellow mixture was concentrated under reduced pressure at 35 + 5 0C on the rotary evaporator over a period of 8 h, until a volume of 45 L (9.0 vol) was achieved. The concentrate was stored under N2 at 2-8 °C.The concentrate was transferred to a 200-L reactor and stirring commenced. Water (45 L, 9.0 vol) was added and the resulting dilute suspension was stirred for 55 min. The batch was transferred portionwise to a 72-L reactor assembled in a heating mantle equipped for vacuum distillation. Distillation at 35 +/- 5 °C commenced and proceeded until a batch volume of 62 L (12.4 vol) was achieved (The distillation was conducted over a period of two days, and included 15 hours of aging at <30 0C once complete). The batch was transferred to a 72-L reactor assembled in a cooling bath. The batch was chilled over a period of A1A h until the temperature reached <5 0C and was stirred for an additional 1 h. The solids were filtered employing Sharkskin filter paper and the cake was rinsed with chilled 2:1 water/acetone (7.5 L, 1.5 vol) (The total filtration time was approximately 1 hour 40 minutes and included pulling N2 through the cake in order to help it dry). The damp solids (5.99 kg) were transferred into six glass <n="32"/>drying trays and dried under vacuum, in an oven at 40 +/- 5 0C. After drying for 47 h, the batch was packaged in 4-mil LDPE (double bags) under N2 and stored in a fiber drum. This afforded 6-chloropurine-9-riboside acetonide (4505 g, 79percent).
76% With toluene-4-sulfonic acid In acetone at 20℃; for 4 h; Inert atmosphere A mixture of 6-chloropurine riboside (1) (1.0 g, 3.5 mmol), p-toluenesulfonic acid monohydrate (1.0 g, 5.3 mmol) and 2,2-dimethoxypropane (10 mL) in acetone (20 mL) was stirred at room temperature under N2 for 3 h. Another portion of 2,2-dimethoxypropane (10 mL) was added, and the mixture was stirred for another 1 h. The mixture was concentrated by rotary evaporation under reduced pressure. The residue was diluted with CH2C12, and extracted with water. The aqueous phase was washed with CH2C12, and the combined organic layers were washed with saturated NaHCO3 and brine. The organic phase was dried over MgSO4, filtered, concentrated by rotatory evaporation under reduced pressure, and purified by column chromatography (silica gel, EtOAc/hexane gradients from 3:7 to 1:0) to give compound 23 (870 mg, 76percent yield). C,3H,5C1N404; [cx]D25 = —112.6 (CHC13, c = 2); JR Vx (neat) 1592, 1563, 1490, 1438, 1419, 1400, 1384, 1337, 1259, 1202, 1154, 1136, 1108, 1080 cm-’; ‘H NMR (CDC13, 600 MHz) ö 8.79 (1 H, s), 8.25 (1 H, s), 6.00 (1 H, d, J= 4.6 Hz), 5.24—5.21 (1 H, m), 5.14 (1 H, dd, J 5.6, 1.5 Hz), 4.93 (1 H, dd, J 10.6, 2.0 Hz), 4.57 (1 H, d, J= 1.5 Hz), 4.00 (1 H, dt, J 12.7, 2.0 Hz), 3.84 (1 H, ddd, J 12.7, 10.6, 2.3 Hz), 1.68 (3 H, s), 1.41 (3 H, s); ‘3C NMR (CDC13, 150 MHz) ö 152.4, 151.7, 150.4, 144.7, 133.4, 114.5,94.1, 86.3, 83.2, 81.5, 63.2, 27.6, 25.2; ESJ—HRMS calcd. for C13H1635C1N404: 327.0855, found: m/z327.0868 [M + Hj.
2.24 g With (R)-10-camphorsulfonic acid In acetone at 20℃; for 11 h; First step, 6-chloropurine riboside (2.0 g) and 2,2-dimethoxypropane (5.80 g) in dry acetone (100 ml), (1S)-(+)-camphor-10-sulfonic acid (1.60 g) was added as a catalyst. The reaction mixture was stirred at room temperature for 11 h. After evaporating the solvent, the mixture was dissolved in chloroform (200 ml), and a NaHCO3 solution (3*30 ml) was added. The water layer was extracted with chloroform (30 ml), then the chloroform layer was dried by anhydrous sodium sulfate and filtered. After evaporation of the solvent, the mixture was separated by column chromatography over silica gel eluting with CHCl3-CH3OH (100:1) to yield 2',3'-O-isopropylidene-6-chloropurine riboside (2.24 g) as a white solid.

Reference: [1] Patent: WO2006/84281, 2006, A1, . Location in patent: Page/Page column 78-79
[2] Journal of the American Chemical Society, 2013, vol. 135, # 45, p. 16948 - 16962
[3] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5433 - 5440
[4] Patent: US2017/312284, 2017, A1, . Location in patent: Paragraph 0093; 0098
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2470 - 2473
[6] Patent: KR2015/10195, 2015, A, . Location in patent: Paragraph 0221-0224
[7] Journal of Medicinal Chemistry, 1990, vol. 33, # 9, p. 2545 - 2551
[8] Molecules, 2012, vol. 17, # 11, p. 13036 - 13044
[9] Patent: US2015/376611, 2015, A1, . Location in patent: Paragraph 0474; 0475
[10] Patent: US2017/354673, 2017, A1, . Location in patent: Paragraph 0690; 0691
[11] ChemMedChem, 2011, vol. 6, # 8, p. 1390 - 1400
[12] Patent: WO2008/111082, 2008, A1, . Location in patent: Page/Page column 30-31; 36
[13] Patent: WO2018/140734, 2018, A1, . Location in patent: Paragraph 00138
[14] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6736 - 6739
[15] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 6, p. 695 - 698
[16] Patent: EP1589027, 2005, A1, . Location in patent: Page/Page column 18-19
[17] Patent: US5824657, 1998, A,
[18] Patent: EP2511283, 2012, A1, . Location in patent: Page/Page column 67
[19] Patent: US2013/45942, 2013, A1, . Location in patent: Paragraph 0258; 0266
  • 3
  • [ 2004-06-0 ]
  • [ 892-48-8 ]
Reference: [1] Patent: WO2017/218802, 2017, A1,
  • 4
  • [ 108-24-7 ]
  • [ 2004-06-0 ]
  • [ 5987-73-5 ]
Reference: [1] Chemistry - A European Journal, 2017, vol. 23, # 59, p. 14702 - 14706
[2] Organic Letters, 2015, vol. 17, # 6, p. 1513 - 1516
Recommend Products
Same Skeleton Products
Historical Records