* 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.
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 6, p. 695 - 698
2
[ 108-24-7 ]
[ 58-63-9 ]
[ 3181-38-2 ]
Yield
Reaction Conditions
Operation in experiment
82%
With dmap; triethylamine In acetonitrile at 20℃; for 1 h;
To a suspension of inosine (1 Og, 37. 3mmol) and catalytic DMAP in MeCN (60mL) was added Et3N (20mL, 143mmol) and acetic anhydride (12.5mL) and the resulting solution was stirred for 1h at ambient temperature before the addition of MeOH (5mL). After stirring for 5mins, the solution was concentrated in vacuo to yield a white solid which was washed with isopropyl alcohol to afford triacetoxy inosine (12. 1g, 82percent).
Reference：
[1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 3, p. 462 - 470
[2] Synthesis, 2003, # 17, p. 2639 - 2642
[3] Journal of the American Chemical Society, 1997, vol. 119, # 32, p. 7423 - 7433
[4] Journal of Organic Chemistry, 1985, vol. 50, # 15, p. 2664 - 2667
[5] Chemistry - A European Journal, 2015, vol. 21, # 33, p. 11634 - 11643
[6] Synlett, 2006, # 20, p. 3474 - 3478
[7] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 5, p. 859 - 866
[8] Journal of applied chemistry of the USSR, 1984, vol. 57, # 9 pt 2, p. 1991 - 1992
[9] Patent: WO2005/54269, 2005, A1, . Location in patent: Page/Page column 14
[10] Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 782 - 793
[11] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 11, p. 2937 - 2942
[12] Journal of Labelled Compounds and Radiopharmaceuticals, 2000, vol. 43, # 1, p. 11 - 28
[13] Monatshefte fur Chemie, 2003, vol. 134, # 6, p. 851 - 873
[14] Patent: EP2407474, 2012, A1, . Location in patent: Page/Page column 5
[15] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6248 - 6263
3
[ 2466-76-4 ]
[ 58-63-9 ]
[ 3181-38-2 ]
Yield
Reaction Conditions
Operation in experiment
70%
With sodium hydroxide In water at 20℃; for 4 h;
General procedure: Nucleoside/nucleotide (2; 100 mM) and N-acetyl imidazole (1a;10 equiv) were dissolved in water (pH 8; adjusted with 4 MNaOH). The solution was incubated at r.t. for 4 h, and NMR spectra were periodically acquired. The product was purified byreverse-phase (C18) flash coumn chromatography (eluted at pH4 with 100 mM NH4HCO2/MeCN = 98:2 to 80:20). The fractions containing 5 were lyophilised to yield a white powder.
Reference：
[1] Journal of Organic Chemistry, 2013, vol. 78, # 12, p. 5832 - 5842
5
[ 1441063-52-0 ]
[ 112-55-0 ]
[ 63067-62-9 ]
[ 3181-38-2 ]
Reference：
[1] Journal of Organic Chemistry, 2013, vol. 78, # 12, p. 5832 - 5842
6
[ 5987-73-5 ]
[ 16645-06-0 ]
[ 31199-61-8 ]
[ 3181-38-2 ]
Reference：
[1] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 1887 - 1894
7
[ 863033-41-4 ]
[ 3181-38-2 ]
Reference：
[1] Chemical Communications, 2005, # 31, p. 3968 - 3970
8
[ 41623-91-0 ]
[ 3181-38-2 ]
Reference：
[1] Journal of the Chemical Society, Chemical Communications, 1989, # 2, p. 1769 - 1770
9
[ 87781-93-9 ]
[ 3181-38-2 ]
Reference：
[1] Journal of the Chemical Society, Chemical Communications, 1989, # 2, p. 1769 - 1770
10
[ 127244-78-4 ]
[ 3181-38-2 ]
Reference：
[1] Journal of the Chemical Society, Chemical Communications, 1989, # 2, p. 1769 - 1770
11
[ 127211-14-7 ]
[ 3181-38-2 ]
Reference：
[1] Journal of the Chemical Society, Chemical Communications, 1989, # 2, p. 1769 - 1770
12
[ 127218-16-0 ]
[ 3181-38-2 ]
Reference：
[1] Journal of the Chemical Society, Chemical Communications, 1989, # 2, p. 1769 - 1770
13
[ 13035-61-5 ]
[ 3181-38-2 ]
Reference：
[1] Journal of the Chemical Society, Chemical Communications, 1989, # 2, p. 1769 - 1770
14
[ 5987-74-6 ]
[ 3181-38-2 ]
Reference：
[1] Journal of Organic Chemistry, 1984, vol. 49, # 23, p. 4340 - 4344
15
[ 3181-38-2 ]
[ 5987-73-5 ]
Yield
Reaction Conditions
Operation in experiment
100%
With N-benzyl-N,N,N-triethylammonium chloride; <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate In acetonitrile at 70℃; for 2 h;
2,3,5-Tri-O-acetylinosine [4] (5.00g, 12.68 mmol, 1.00 equiv), benzyltriethylammonium chloride (5.77 g, 25.36 mmol, 2.00 equiv) andN,N-dimethylaniline (1.8 mL, 13.94 mmol, 1.10 equiv) were dissolved in 50 mL dry acetonitrile. Theflask was placed on a preheated oil bath (70 °C), POCl3 (5.9 mL, 63.40 mmol, 5.00 equiv) was addedslowly and the reaction mixture was stirred for 2 h at the same temperature. After that, the solvent andexcess POCl3 were removed under reduced pressure (high vacuum, 70 °C). The residue was pouredon a CHCl3/ice-mixture and the solution was stirred for 20 min. The organic phase was separated andthe aqueous phase was extracted 3 times with CHCl3. The organic phases were combined and washedwith a 5 percent NaHCO3 solution until the aqueous layer showed a slightly basic reaction. Subsequentlythe organic phase was separated, dried with MgSO4 and the solvent was removed under reducedpressure. Purification by silica gel chromatography (EtOAc) gave compound 17 as a yellow oil (5.23g, quant.)
Reference：
[1] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 1563 - 1569
[2] Russian Journal of Bioorganic Chemistry, 1999, vol. 25, # 9, p. 603 - 611
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6736 - 6739
[4] Patent: WO2005/84653, 2005, A2, . Location in patent: Page/Page column 42
[5] British Journal of Pharmacology, 2017, vol. 174, # 14, p. 2287 - 2301
[6] Patent: WO2005/84653, 2005, A2, . Location in patent: Page/Page column 42
16
[ 3181-38-2 ]
[ 5987-73-5 ]
Yield
Reaction Conditions
Operation in experiment
96%
With thionyl chloride; N,N-dimethyl-formamide In chloroform
To a solution of triacetoxy inosine (3. 00g, 7. 63mol) in CHC13 (25mL) was added DMF (1. 80mL, 22.9mmol) and thionyl chloride (1. 68mL, 22. 9mmol) and the resulting solution was refluxed overnight before removal of the solvents in vacuo. The residue was then partitioned between DCM and aq. NaHCO3 and the separated organic phase was washed with brine and dried over MgS04 to afford triacetoxy 6-chloroadenosine as apale yellow oil (3.03g, 96percent).
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 11, p. 2937 - 2942
[2] Tetrahedron Letters, 2000, vol. 41, # 11, p. 1695 - 1697
[3] Organic and Biomolecular Chemistry, 2005, vol. 3, # 3, p. 462 - 470
[4] Patent: WO2005/54269, 2005, A1, . Location in patent: Page/Page column 14
[5] Monatshefte fur Chemie, 2003, vol. 134, # 6, p. 851 - 873
[6] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 6, p. 695 - 698
[7] Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 782 - 793
[8] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 7, p. 534 - 537
[9] Journal of Organic Chemistry, 1985, vol. 50, # 15, p. 2664 - 2667
[10] Journal of Medicinal Chemistry, 1985, vol. 28, # 11, p. 1636 - 1643
[11] Journal of Labelled Compounds and Radiopharmaceuticals, 2000, vol. 43, # 1, p. 11 - 28
[12] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 5, p. 859 - 866
[13] Patent: EP2407474, 2012, A1, . Location in patent: Page/Page column 5
[14] Journal of Medicinal Chemistry, 2012, vol. 55, # 18, p. 8066 - 8074,9
[15] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6248 - 6263
Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-[6-(2-propyl-imidazol-1-yl)-purin-9-yl]-tetrahydro-furan-3-yl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With iodine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In toluene; at 95℃; for 4h;
Preparation of 6-(2-propylimidazol-l -vDpurine. A suspension of 2',3',5'-tri-O-acetylinosine (1.58 g, 4.0 mmol), 2- propylimidazole (1.60 g, 14.4 mmol), Ph3P (2.58 g, 9.6 mmol), I2 (2.14 g, 8.32 mmol), and EtN(Z-Pr)2 (3.6 mL, 2.67 g, 20.2 mmol) in dried toluene (40 mL) was stirred at 95 C for 4 h. Volatiles were evaporated in vacuo, and the residue was extracted with boiling EtOAc. The combined extracts were evaporated to dryness, and the residue was chromatographed (CH2Cl2ZMeOH, 1 :40) to give a solid contaminated with Ph3PO. This material was dissolved in AcOH (160 mL), and AcCl (2.2 mL, 2.43 g, 31 mmol) was added. The solution was stirred at 65 C overnight, and volatiles were evaporated in vacuo. The residue was dissolved in CH2Cl2 and extracted with 0.1 N NaOHZH2O. The aqueous layer was washed (CH2Cl2), and precipitation with CO2 followed by filtration and thorough washing (H2O) gave a solid (0.66 g, 72%). This material was dissolved in MeOH and decolorized with charcoal. Recrystallization (MeOH) gave 6-(2-propylimidazol-l- yl)purine as a colorless solid: mp 242.5-243.5 C; UV (MeOH) max 278 nm (epsilon 13 700), min 235 nm (epsilon 5000); 1H NMR (300 MHz5 DMSO-^6) delta 13.90 (br s, IH), 8.86 (s, IH), 8.69 (s, IH), 8.36 (s, IH), 7.07 (d, J= 1.5 Hz, IH), 3.18 (t, J= 7.3 Hz, 2H), 1.72 (sext, J= 7.3 Hz, 2H), 0.93 (t, J= 7.3 Hz, 3H); 13C NMR (75 MHz, CDCl3) delta 155.5, 152.0, 149.8, 146.9, 145.8, 128.5, 123.6, 121.4, 32.2, 21.5, 14.5; HRMS m/z 228.1109 (M+ [C11H12N6] = 228.1123). Anal. Calcd for CnH12N6: C, 57.88; H, 5.30; N, 36.82. Found: C, 58.09; H, 5.19; N, 37.00.
N-(4-(9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)-9H-purin-6-ylamino)butyl)-6-(2-(4-(2-(4,4-difluoro-4,4a-dihydro-5-(thiophen-2-yl)-4-bora-3a,4a-diaza-s-indacene-3-yl)vinyl)phenoxy)acetamido)hexanamide[ No CAS ]
(R)-3-[(3aR,4R,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-8-phenyl-7,8-dihydro-3H-imidazo[2,1-i]purine[ No CAS ]
(S)-3-[(3aR,4R,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-8-phenyl-7,8-dihydro-3H-imidazo[2,1-i]purine[ No CAS ]
(R)-8-Benzyl-3-[(3aR,4R,6R,6aR)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-7,8-dihydro-3H-imidazo[2,1-i]purine[ No CAS ]
(S)-8-Benzyl-3-[(3aR,4R,6R,6aR)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-7,8-dihydro-3H-imidazo[2,1-i]purine[ No CAS ]
(7R,8R)-3-[(3aR,4R,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-8-methyl-7-phenyl-7,8-dihydro-3H-imidazo[2,1-i]purine[ No CAS ]
(7S,8S)-3-[(3aR,4R,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-8-methyl-7-phenyl-7,8-dihydro-3H-imidazo[2,1-i]purine[ No CAS ]
(1S,2R)-2-{9-[(3aR,4R,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-ylamino}-1-phenyl-propan-1-ol[ No CAS ]
(1R,2S)-2-{9-[(3aR,4R,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-ylamino}-1-phenyl-propan-1-ol[ No CAS ]
(S)-2-{9-[(3aR,4R,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-ylamino}-3-phenyl-propan-1-ol[ No CAS ]
(R)-2-{9-[(3aR,4R,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-ylamino}-3-phenyl-propan-1-ol[ No CAS ]
(S)-2-{9-[(3aR,4R,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-ylamino}-2-phenyl-ethanol[ No CAS ]
(R)-2-{9-[(3aR,4R,6R,6aR)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-ylamino}-2-phenyl-ethanol[ No CAS ]
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
