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Chemistry
Organic Building Blocks
Tetrahydrofurans
methylthiomethyl
5'-Methylthioadenosine
Chemistry
Life Science
Organic Building Blocks
Heterocyclic Building Blocks DNA/RNA
Tetrahydrofurans
Purines Thiols Nucleosides and Nucleotides
methylthiomethyl
9-(tetrahydrofuran-2-yl)-9H-purin-6-amine

[ CAS No. 2457-80-9 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 2457-80-9
Chemical Structure| 2457-80-9
Structure of 2457-80-9 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 2457-80-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2457-80-9 ]

SDS Specification
Alternatived Products of [ 2457-80-9 ]

Product Details of [ 2457-80-9 ]

CAS No. :2457-80-9 MDL No. :MFCD00010533
Formula : C11H15N5O3S Boiling Point : -
Linear Structure Formula :- InChI Key :WUUGFSXJNOTRMR-IOSLPCCCSA-N
M.W : 297.33 Pubchem ID :439176
Synonyms :
Chemical Name :(2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol

Calculated chemistry of [ 2457-80-9 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.55
Num. rotatable bonds : 3
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 73.91
TPSA : 144.61 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) : -8.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.27
Log Po/w (XLOGP3) : -0.27
Log Po/w (WLOGP) : -0.93
Log Po/w (MLOGP) : -1.25
Log Po/w (SILICOS-IT) : -1.33
Consensus Log Po/w : -0.5

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.65
Solubility : 6.68 mg/ml ; 0.0225 mol/l
Class : Very soluble
Log S (Ali) : -2.31
Solubility : 1.46 mg/ml ; 0.00492 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.65
Solubility : 66.1 mg/ml ; 0.222 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.12

Safety of [ 2457-80-9 ]

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 [ 2457-80-9 ]

* 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 [ 2457-80-9 ]

[ 2457-80-9 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 2457-80-9 ]
  • [ 74-88-4 ]
  • [ 81162-88-1 ]
YieldReaction ConditionsOperation in experiment
With acetic acid
With formic acid
With formic acid at 40℃;
Reference： [1]Parks; Schlenk [Journal of Biological Chemistry, 1958, vol. 230, p. 295,298]
[2]Mudd [Journal of Biological Chemistry, 1959, vol. 234, p. 87,88]
[3]Guerard, Christine; Breard, Maud; Courtois, Fabienne; Drujon, Thierry; Ploux, Olivier [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 7, p. 1661 - 1664]
  • 2
  • [ 2457-80-9 ]
  • [ 23656-67-9 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid
With hydrogenchloride
Reference： [1]Levene; Sobotka [Journal of Biological Chemistry, 1925, vol. 65, p. 551,554] Suzuki; Mori [Biochemische Zeitschrift, 1925, vol. 162, p. 413,417] Suzuki et al. [Biochemische Zeitschrift, 1924, vol. 154, p. 278,279][Nippon Nogei Kagaku Kaishi, 1924, vol. 1, p. 127,128] Levene [Journal of Biological Chemistry, 1924, vol. 59, p. 465,469]
[2]Levene; Sobotka [Journal of Biological Chemistry, 1925, vol. 65, p. 551,554] Suzuki; Mori [Biochemische Zeitschrift, 1925, vol. 162, p. 413,417] Suzuki et al. [Biochemische Zeitschrift, 1924, vol. 154, p. 278,279][Nippon Nogei Kagaku Kaishi, 1924, vol. 1, p. 127,128] Levene [Journal of Biological Chemistry, 1924, vol. 59, p. 465,469]
  • 3
  • [ 2457-80-9 ]
  • [ 17298-58-7 ]
YieldReaction ConditionsOperation in experiment
93% With phosphate buffer pH 6.8; ethanethiol In water α-amylase from Aspergillus oryzae;
With acetic acid; sodium nitrite
With adenosine deaminase from Plasmodium falciparum In phosphate buffer at 30℃; Enzymatic reaction;
With adenosine deaminase from Bovine taurus In phosphate buffer at 30℃; Enzymatic reaction;
With adenosine deaminase from Homo sapiens In phosphate buffer at 30℃; Enzymatic reaction;
With Sav2595 from Steptomyces avermitilis MA-4680; water at 30℃; for 16h; Enzymatic reaction;

Reference： [1]Wnuk; Stoeckler; Robins [Nucleosides and Nucleotides, 1994, vol. 13, # 1-3, p. 389 - 403]
[2]Kuhn; Henkel [Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1941, vol. 269, p. 41,45] SATOH; MAKINO [Nature, 1951, vol. 167, # 4241, p. 238 - 238] Satoh [Journal of Biochemistry, 1953, vol. 40, p. 563,567]
[3]Tyler, Peter C.; Taylor, Erika A.; Froehlich, Richard F. G.; Schramm, Vern L. [Journal of the American Chemical Society, 2007, vol. 129, # 21, p. 6872 - 6879]
[4]Tyler, Peter C.; Taylor, Erika A.; Froehlich, Richard F. G.; Schramm, Vern L. [Journal of the American Chemical Society, 2007, vol. 129, # 21, p. 6872 - 6879]
[5]Tyler, Peter C.; Taylor, Erika A.; Froehlich, Richard F. G.; Schramm, Vern L. [Journal of the American Chemical Society, 2007, vol. 129, # 21, p. 6872 - 6879]
[6]Goble, Alissa M.; Toro, Rafael; Li, Xu; Ornelas, Argentina; Fan, Hao; Eswaramoorthy, Subramaniam; Patskovsky, Yury; Hillerich, Brandan; Seidel, Ron; Sali, Andrej; Shoichet, Brian K.; Almo, Steven C.; Swaminathan, Subramanyam; Tanner, Martin E.; Raushel, Frank M. [Biochemistry, 2013, vol. 52, # 37, p. 6525 - 6536]
  • 4
  • [ 69660-30-6 ]
  • [ 2457-80-9 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid
With sulfuric acid; acetone
With sulfuric acid; acetic acid
Reference： [1]Satoh [Journal of Biochemistry, 1953, vol. 40, p. 563,567]
[2]Weygand; Trauth [Chemische Berichte, 1951, vol. 84, p. 633]
[3]Baddiley [Journal of the Chemical Society, 1951, p. 1348,1351] Baddiley; Jamieson [Journal of the Chemical Society, 1954, p. 4280,4283]
  • 5
  • [ 108-24-7 ]
  • [ 2457-80-9 ]
  • [ 119771-17-4 ]
YieldReaction ConditionsOperation in experiment
98% With pyridine at 0℃; for 7h;
87% With pyridine at 0 - 10℃; for 6h; 1.1b Synthetic procedure: 5'-S~methyl-5'~thio- Adenosine (1 .0 gr, 0.0033 mole, 1 .0 mole eq.) and anhydrous pyridine ( 10 mi) were placed in an oven dried, 50 ml three neck flask, equipped with a dropping funnel, inert gas inlet/outlet and a thermometer. The reaction set was placed in an ice/salt bath and agitation was initiated. When the temperature of the solution dropped to 0 °C, acetic anhydride (10 mi, 0.105 mole, 31.8 mole eq.) was added drop-wise for 15 minutes and the temperature of the reaction mixture was maintained below 5 "C during acetic anhydride addition. The reaction mixture was stirred for 6 hours at 5-10 °C. Quenched the excess acetic anhydride by adding ice-cold water (100 ml), and then pH adjusted to 7 by adding 10 wt% NaHC03 aqueous solution. The aqueous mixture was extracted with ethyl acetate (2 x 100 ml). The combined ethyl acetate extracts are dried over anhydrous Na2S04 (Igr), filtered into a 250 ml round-bottomed flask. Concentrated the filtrate to dryness under reduced pressure at 35-40 °C to give the crude product as a pale yellow syrupy liquid, then pure product was obtained as off-white crystals (1.08 gr, Yield: 87 %, Purity by HPLC: >99%) by passing through a silica gel column with a mixture of ethyl acetate and hexanes (1 :3 v/v).
78% With dmap; triethylamine In acetonitrile for 1h; Ambient temperature;
75% With dmap; triethylamine In acetonitrile for 1h;

Reference： [1]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
[2]Current Patent Assignee: PARSONS BRINCKERHOFF GROUP INC - WO2018/212980, 2018, A1 Location in patent: Paragraph 00221
[3]Guillerm, Georges; Gatel, Marie [Journal of the Chemical Society. Perkin transactions I, 1994, # 2, p. 153 - 154]
[4]Sufrin, Janice R.; Spiess, Arthur J.; Kramer, Debora L.; Libby, Paul R.; Porter, Carl W. [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 997 - 1001]
  • 6
  • [ 2457-80-9 ]
  • [ 98-88-4 ]
  • [ 153815-18-0 ]
YieldReaction ConditionsOperation in experiment
85% With pyridine for 16h; Ambient temperature;
Reference： [1]Guillerm, Georges; Gatel, Marie [Journal of the Chemical Society. Perkin transactions I, 1994, # 2, p. 153 - 154]
  • 7
  • [ 2457-80-9 ]
  • [ 74-88-4 ]
  • dimethyl(5'-adenosyl)sulfonium perchlorate [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.1% With formic acid for 72h; Ambient temperature;
Reference： [1]Tang; Mariuzza; Coward [Journal of Medicinal Chemistry, 1981, vol. 24, # 11, p. 1277 - 1284]
  • 8
  • [ 2457-80-9 ]
  • [ 4754-39-6 ]
YieldReaction ConditionsOperation in experiment
83% With hydrogen; nickel In water at 90℃; for 48h;
Reference： [1]Scovill, John P.; Thigpen, Don L.; Lemley, Paul V. [Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 85, # 1-4, p. 149 - 152]
  • 9
  • [ 74-93-1 ]
  • [ 892-48-8 ]
  • [ 2457-80-9 ]
Reference： [1]Canadian Journal of Chemistry,1991,vol. 69,p. 1468 - 1474
[2]Phosphorus, Sulfur and Silicon and the Related Elements,1993,vol. 85,p. 149 - 152
[3]Tetrahedron Letters,1988,vol. 29,p. 5729 - 5732
[4]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2829 - 2833
  • 10
  • [ 83332-24-5 ]
  • [ 2457-80-9 ]
  • [ 134461-75-9 ]
YieldReaction ConditionsOperation in experiment
With amine buffer In water at 40℃; pH > 10;
Reference： [1]Vasquez, Peter J.; Coward, James K. [Journal of the Chemical Society. Chemical communications, 1982, # 12, p. 698 - 699]
  • 11
  • [ 624-92-0 ]
  • [ 58-61-7 ]
  • [ 2457-80-9 ]
YieldReaction ConditionsOperation in experiment
38% With tributylphosphine In N,N-dimethyl-formamide for 240h;
Reference： [1]Nakagawa, Iwao; Aki, Koichi; Hata, Tsujiaki [Journal of the Chemical Society. Perkin transactions I, 1983, # 7, p. 1315 - 1318]
YieldReaction ConditionsOperation in experiment
With extractene from cultures of yeast
With aerobacter aerogenes
YieldReaction ConditionsOperation in experiment
With water pH 4-6;
  • 14
  • [ 2457-80-9 ]
  • 5'-deoxy-5'-methylthioinosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With adenylate deaminase; dimethyl sulfoxide In phosphate buffer for 0.05h;
Reference： [1]Ciuffreda, Pierangela; Loseto, Angela; Alessandrini, Laura; Terraneo, Giancarlo; Santaniello, Enzo [European Journal of Organic Chemistry, 2003, # 24, p. 4748 - 4751]
  • 15
  • [ 892-48-8 ]
  • [ 5188-07-8 ]
  • [ 2457-80-9 ]
Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 3857 - 3861
    Angew. Chem.,2017,vol. 129,p. 3915 - 3919,5
[2]European Journal of Organic Chemistry,2003,p. 4748 - 4751
  • 16
  • [ 2457-80-9 ]
  • [ 77-76-9 ]
  • [ 69660-30-6 ]
YieldReaction ConditionsOperation in experiment
99% With toluene-4-sulfonic acid In acetone at 20℃; for 2h;
Reference： [1]Steere, Jennifer A.; Honek, John F. [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 15, p. 3229 - 3236]
  • 17
  • [ 2457-80-9 ]
  • (2S,3R,4S,5S)-2-Methoxy-5-methylsulfanylmethyl-tetrahydro-furan-3,4-diol [ No CAS ]
  • (2R,3R,4S,5S)-2-Methoxy-5-methylsulfanylmethyl-tetrahydro-furan-3,4-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 15% 2: 40% With trifluoroacetic acid In methanol Heating;
Reference： [1]Turnbull, W. Bruce; Shimizu, Kazumi Hiruma; Chatterjee, Delphi; Homans, Steve W.; Treumann, Achim [Angewandte Chemie - International Edition, 2004, vol. 43, # 30, p. 3918 - 3922]
  • 18
  • [ 2457-80-9 ]
  • (2S,3S,4S)-1-(6-Amino-purin-9-yl)-5-methylsulfanyl-pentane-2,3,4-triol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 99 percent / p-toluenesulfonic acid monohydrate / acetone / 2 h / 20 °C 2: 17 percent / diisobutylaluminum hydride / tetrahydrofuran / 24 h / 20 °C 3: 97 percent / trifluoroacetic acid; water / 1.5 h / 20 °C
Reference： [1]Steere, Jennifer A.; Honek, John F. [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 15, p. 3229 - 3236]
  • 19
  • [ 2457-80-9 ]
  • 9-(5'-deoxy-2',3'-O-isopropylidene-5'-thiomethyl-D-ribityl)adenine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 99 percent / p-toluenesulfonic acid monohydrate / acetone / 2 h / 20 °C 2: 17 percent / diisobutylaluminum hydride / tetrahydrofuran / 24 h / 20 °C
Reference： [1]Steere, Jennifer A.; Honek, John F. [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 15, p. 3229 - 3236]
  • 20
  • [ 662131-88-6 ]
  • [ 2457-80-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 98 percent / water; methanol / 20 °C 2: 50 percent / dimethylformamide / 20 °C
Multi-step reaction with 2 steps 1: conc. aq. NH4OH / methanol / 1 h / Ambient temperature 2: 75 percent / NaOH / H2O; methanol / 24 h / 75 °C
Reference： [1]Ciuffreda, Pierangela; Loseto, Angela; Alessandrini, Laura; Terraneo, Giancarlo; Santaniello, Enzo [European Journal of Organic Chemistry, 2003, # 24, p. 4748 - 4751]
[2]Scovill, John P.; Thigpen, Don L.; Lemley, Paul V. [Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 85, # 1-4, p. 149 - 152]
  • 21
  • [ 2457-80-9 ]
  • [ 119771-16-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C
Multi-step reaction with 2 steps 1: 78 percent / DMAP, NEt3 / acetonitrile / 1 h / Ambient temperature 2: XeF2 / CH2Cl2 / 6 h / -60 °C
Reference： [1]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
[2]Guillerm, Georges; Gatel, Marie [Journal of the Chemical Society. Perkin transactions I, 1994, # 2, p. 153 - 154]
  • 22
  • [ 2457-80-9 ]
  • [ 119771-18-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: (diethylamido)sulfur trifluoride / SbCl3 / CH2Cl2 / 10 h / Ambient temperature
Multi-step reaction with 2 steps 1: 78 percent / DMAP, NEt3 / acetonitrile / 1 h / Ambient temperature 2: 70 percent / XeF2 / CH2Cl2 / 6 h / -60 °C
Multi-step reaction with 2 steps 1: 1.) pyridine, 2.) MCPBA / 2.) CH2Cl2, -40 deg C 2: diethylaminosulfur trichloride, SbCl3 / CH2Cl2 / Ambient temperature
Reference： [1]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
[2]Guillerm, Georges; Gatel, Marie [Journal of the Chemical Society. Perkin transactions I, 1994, # 2, p. 153 - 154]
[3]Robins; Wnuk [Tetrahedron Letters, 1988, vol. 29, # 45, p. 5729 - 5732]
  • 23
  • [ 2457-80-9 ]
  • [ 118560-47-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: 1.) (diethylamido)sulfur trifluoride, 2.) NH3 / 1.) SbCl3 / 1.) CH2Cl2, r.t., 10 h, 2.) r.t., 2 h
Multi-step reaction with 3 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: 1.) (diethylamido)sulfur trifluoride, 2.) NH3 / 1.) SbCl3 / 1.) CH2Cl2, r.t., 10 h, 2.) MeOH, r.t., 2 h
Multi-step reaction with 3 steps 1: 78 percent / DMAP, NEt3 / acetonitrile / 1 h / Ambient temperature 2: 70 percent / XeF2 / CH2Cl2 / 6 h / -60 °C 3: Na2CO3 / methanol / 15 h / Ambient temperature
Multi-step reaction with 3 steps 1: 85 percent / pyridine / 16 h / Ambient temperature 2: 75 percent / XeF2 / CH2Cl2 / 6 h / -60 °C 3: Na2CO3 / methanol / 15 h / Ambient temperature
Multi-step reaction with 2 steps 1: 1.) pyridine, 2.) MCPBA / 2.) CH2Cl2, -40 deg C 2: 1.) diethylaminosulfur trifluoride, SbCl3, 2.) NH3 / 1.) CH2Cl2, room temp; 2.) MeOH

Reference： [1]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
[2]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
[3]Guillerm, Georges; Gatel, Marie [Journal of the Chemical Society. Perkin transactions I, 1994, # 2, p. 153 - 154]
[4]Guillerm, Georges; Gatel, Marie [Journal of the Chemical Society. Perkin transactions I, 1994, # 2, p. 153 - 154]
[5]Robins; Wnuk [Tetrahedron Letters, 1988, vol. 29, # 45, p. 5729 - 5732]
  • 24
  • [ 2457-80-9 ]
  • 9-<5(E)-O-Methyl-β-D-erythro-pent-4-enofuranosyl>adenine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: 1.) (diethylamido)sulfur trifluoride, 2.) NH3 / 1.) SbCl3 / 1.) CH2Cl2, r.t., 10 h, 2.) r.t., 2 h 4: pyridine / 7 h / 0 °C 5: EtN(i-Pr)2 / bis-(2-methoxy-ethyl) ether / 3.5 h / Heating 6: NH3 / methanol / 2 h / Ambient temperature
Multi-step reaction with 6 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: 1.) (diethylamido)sulfur trifluoride, 2.) NH3 / 1.) SbCl3 / 1.) CH2Cl2, r.t., 10 h, 2.) MeOH, r.t., 2 h 4: pyridine / 7 h / 0 °C 5: EtN(i-Pr)2 / bis-(2-methoxy-ethyl) ether / 3.5 h / Heating 6: NH3 / methanol / 2 h / Ambient temperature
Reference： [1]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
[2]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
  • 25
  • [ 2457-80-9 ]
  • 5'-O-methyl-5'-(methylthio)adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: 1.) (diethylamido)sulfur trifluoride, 2.) NH3 / 1.) SbCl3 / 1.) CH2Cl2, r.t., 10 h, 2.) r.t., 2 h
Multi-step reaction with 3 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: 1.) (diethylamido)sulfur trifluoride, 2.) NH3 / 1.) SbCl3 / 1.) CH2Cl2, r.t., 10 h, 2.) MeOH, r.t., 2 h
Reference： [1]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
[2]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
  • 26
  • [ 2457-80-9 ]
  • [ 153920-19-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: 1.) (diethylamido)sulfur trifluoride, 2.) NH3 / 1.) SbCl3 / 1.) CH2Cl2, r.t., 10 h, 2.) r.t., 2 h 4: pyridine / 7 h / 0 °C 5: EtN(i-Pr)2 / bis-(2-methoxy-ethyl) ether / 3.5 h / Heating
Multi-step reaction with 5 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: 1.) (diethylamido)sulfur trifluoride, 2.) NH3 / 1.) SbCl3 / 1.) CH2Cl2, r.t., 10 h, 2.) MeOH, r.t., 2 h 4: pyridine / 7 h / 0 °C 5: EtN(i-Pr)2 / bis-(2-methoxy-ethyl) ether / 3.5 h / Heating
Reference： [1]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
[2]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
  • 27
  • [ 2457-80-9 ]
  • 2',3'-Di-O-acetyl-5'-O-methyl-5'-(methylthio)adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: 1.) (diethylamido)sulfur trifluoride, 2.) NH3 / 1.) SbCl3 / 1.) CH2Cl2, r.t., 10 h, 2.) r.t., 2 h 4: pyridine / 7 h / 0 °C
Multi-step reaction with 4 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: 1.) (diethylamido)sulfur trifluoride, 2.) NH3 / 1.) SbCl3 / 1.) CH2Cl2, r.t., 10 h, 2.) MeOH, r.t., 2 h 4: pyridine / 7 h / 0 °C
Reference： [1]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
[2]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
  • 28
  • [ 2457-80-9 ]
  • 2',3'-Di-O-acetyl-5'(R)-fluoro-5'-S-methyl-5'-thioadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: (diethylamido)sulfur trifluoride / SbCl3 / CH2Cl2 / 10 h / Ambient temperature
Multi-step reaction with 2 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: XeF2 / CH2Cl2 / 1.) -25 deg C to r.t., 1 h, 2.) r.t., 30 min
Reference： [1]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
[2]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
  • 29
  • [ 2457-80-9 ]
  • 2',3'-Di-O-acetyl-5'(S)-fluoro-5'-S-methyl-5'-thioadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: 86 percent / MCPBA / CH2Cl2 / 0.5 h / -50 °C 3: (diethylamido)sulfur trifluoride / SbCl3 / CH2Cl2 / 10 h / Ambient temperature
Multi-step reaction with 2 steps 1: 98 percent / pyridine / 7 h / 0 °C 2: XeF2 / CH2Cl2 / 1.) -25 deg C to r.t., 1 h, 2.) r.t., 30 min
Reference： [1]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
[2]Robins; Wnuk; Mullah; Dalley; Yuan; Lee; Borchardt [Journal of Organic Chemistry, 1994, vol. 59, # 3, p. 544 - 555]
  • 30
  • [ 892-48-8 ]
  • [ 2457-80-9 ]
Reference： [1]Journal of the Chemical Society. Chemical communications,1982,p. 698 - 699
[2]Journal of the Chemical Society. Chemical communications,1982,p. 698 - 699
  • 31
  • [ 3387-65-3 ]
  • [ 2457-80-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 74 percent / 4-(dimethylamino)pyridine, Et3N / acetonitrile / 1 h 2: 1) (dimethylamino)sulfur trifluoride, 2) NH3 / 1) CHCl3, 55 deg C, 2.5-3 h, 2) MeOH, r.t., 2.5 h
Reference： [1]Sufrin, Janice R.; Spiess, Arthur J.; Kramer, Debora L.; Libby, Paul R.; Porter, Carl W. [Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 997 - 1001]
  • 32
  • [ 69260-62-4 ]
  • [ 2457-80-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 94 percent / conc.NH4OH / methanol; H2O / 0.5 h / Ambient temperature 2: 86 percent / NaH / dimethylformamide / -30 deg C to r.t., overnight
Reference： [1]Robins; Hansske; Wnuk; Kanai [Canadian Journal of Chemistry, 1991, vol. 69, # 9, p. 1468 - 1474]
  • 33
  • [ 2457-80-9 ]
  • 2',3'-Di-O-acetyl-5'-deoxy-5'-fluoro-5'-(methylthio)adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) pyridine, 2.) MCPBA / 2.) CH2Cl2, -40 deg C 2: diethylaminosulfur trichloride, SbCl3 / CH2Cl2 / Ambient temperature
Reference： [1]Robins; Wnuk [Tetrahedron Letters, 1988, vol. 29, # 45, p. 5729 - 5732]
  • 34
  • [ 58-61-7 ]
  • [ 2457-80-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) SOCl2, pyridine, 2.) NH3 / 1.) acetonitrile, 2.) MeOH, H2O 2: NaH / dimethylformamide
Multi-step reaction with 4 steps 1: unter Zusatz von ZnCl2 2: pyridine 3: DMF 4: aqueous H2SO4; acetic acid
Multi-step reaction with 4 steps 1: unter Zusatz von ZnCl2 2: pyridine 3: acetone 4: aqueous H2SO4
Reference： [1]Robins; Wnuk [Tetrahedron Letters, 1988, vol. 29, # 45, p. 5729 - 5732]
[2]Baddiley [Journal of the Chemical Society, 1951, p. 1348,1351]
[3]Satoh [Journal of Biochemistry, 1953, vol. 40, p. 563,567]
  • 35
  • sodium salt of methanethiol [ No CAS ]
  • [ 892-48-8 ]
  • [ 2457-80-9 ]
Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1388 - 1407
  • 36
  • [ 74-83-9 ]
  • [ 2457-80-9 ]
  • [ 1106914-63-9 ]
YieldReaction ConditionsOperation in experiment
65% In formic acid; diethyl ether; acetic acid at 20℃; for 144h; Darkness;
Reference： [1]Location in patent: experimental part McCloskey, Diane E.; Bale, Shridhar; Secrist III, John A.; Tiwari, Anita; Moss III, Thomas H.; Valiyaveettil, Jacob; Brooks, Wesley H.; Guida, Wayne C.; Pegg, Anthony E.; Ealick, Steven E. [Journal of Medicinal Chemistry, 2009, vol. 52, # 5, p. 1388 - 1407]
  • 37
  • [ 2457-80-9 ]
  • 5-methylthio-D-ribose [ No CAS ]
  • [ 73-24-5 ]
YieldReaction ConditionsOperation in experiment
Enzymatic reaction; 2 In this study multiple isotopomers of MTA were used to study the transition state of 5% methylthioadenosine/S-adenosylhomocysteine (MTAN) of S. pneumoniae, a bacterial enzyme involved in polyamine biosynthesis, quorum sensing, purine and methionine salvage (Schauder et al., 2001; Ragione et al., 1985; Miller and Duerre, 1968; Tabor and Tabor, 1983; Xavier and Bassler, 2003; Parsek et al., 1999; Withers et al., 2001; Miller et al., 2002). It catalyzes the physiologically irreversible hydrolytic cleavage of the N-glycosidic bonds of 5% methylthioadenosine (MTA) or 5-S-adenosylhomocysteine to 5-methylthioribose, S-ribosylhomocysteine and adenine (FIG. 7). Adenine is salvaged by adenine phosphoribosyltransferase (APRTase) and methylthioribose is converted to methionine in multiple steps (Myers and Abeles, 1989). MTAN has been proposed to be a target for the design of antimicrobial agents because of its involvement in the synthesis of autoinducers2 (AI2). AI2s are quorum sensing molecules formed from S-ribosylhomocysteine and used by bacteria to signal biofilm formation, causing prolonged chronic infections. Mutational studies in Haemophilus influenzae, Streptococcus pneumoniae, Streptococcus pyogenes, and Enterococcus faecalis have suggested that mutations to the pfs gene (pfs gene encodes for MTAN) may reduce pathogenicity and the enzyme has been targeted for the design of antimicrobial agents (Cadieux et al., 2002; Riscoe et al., 1989; Sufrin et al., 1005).
Reference： [1]Current Patent Assignee: MONTEFIORE MEDICAL CENTER - US2011/86812, 2011, A1 Location in patent: Page/Page column 14
  • 38
  • [ 63-68-3 ]
  • [ 56-65-5 ]
  • [ 14031-35-7 ]
  • [ 2457-80-9 ]
Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3965 - 3969
    Angew. Chem.,2014,vol. 53-126,p. 4046 - 4050
  • 39
  • [ 63-68-3 ]
  • [ 56-65-5 ]
  • [ 2457-80-9 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; GLUTATHIONE; human methionine adenosyltransferase plasmid MATI; potassium chloride; magnesium chloride; In aq. buffer; at 23℃; for 0.333333h;pH 8;Enzymatic reaction;Catalytic behavior; Kinetics; A prior HPLC-based MAT activity assay was used to characterize the kinetics of native MATs [25]. This experiment was carried out as an established standard to evaluate the robustness of the newly developed LC-MS/MS-based assay in the current work. Briefly, the activities of native MATs were measured in 2 ml of reaction mixture containing 100 mM Tris-HCl (pH 8.0), 100 mM KCl, 2 mM MgCl2, 8 mM glutathione, 2.5 mM <strong>[56-65-5]ATP</strong>, 7.5 muM MATs, and varied concentrations of methionine (up to 4 mM). The reaction mixture was incubated at ambient temperature (23 C) with a 4 min interval within 20 min (a linear range of initial rates), and then a 300 mul reaction aliquot was quenched with 300 mul of 20% HClO4 aqueous solution. After centrifugation at 15,350 g for 30 min, the supernatants containing SAM were resolved by reverse-phase HPLC using a DELTA PAK C18 column (15 mum, 300×3.9 mm) by monitoring at UV 260 nm. The triethylamine-acetic acid buffer (50 mM, pH 5.0) and methanol were premixed with the ratios of 98:2 (buffer A) and 50:50 (buffer B). SAM was eluted with buffer A for 30 min, followed by buffer B for 5 min, at a flow rate of 1 ml/min. The integrated peak areas at 260 nm were used to generate the standard curve with the known concentration of SAM and to quantify the SAM produced in the kinetic assay (epsilon260=15,400Lmol-1cm-1 for SAM?s adenine moiety).
Reference： [1]Analytical Biochemistry,2014,vol. 450,p. 11 - 19
  • 40
  • 4-bromocrotonic acid [ No CAS ]
  • [ 2457-80-9 ]
  • C15H19N5O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With formic acid; silver perchlorate; acetic acid at 0 - 20℃; for 5.33333h;
Reference： [1]Dong, Min; Horitani, Masaki; Dzikovski, Boris; Pandelia, Maria-Eirini; Krebs, Carsten; Freed, Jack H.; Hoffman, Brian M.; Lin, Hening [Journal of the American Chemical Society, 2016, vol. 138, # 31, p. 9755 - 9758]
  • 41
  • C15H19N5O5S [ No CAS ]
  • [ 2457-80-9 ]
YieldReaction ConditionsOperation in experiment
With Pyrococcus horikoshii Dph2; dithionite(2-) In aq. acetate buffer at 20℃; for 0.333333h; Inert atmosphere; Enzymatic reaction;
Reference： [1]Dong, Min; Horitani, Masaki; Dzikovski, Boris; Pandelia, Maria-Eirini; Krebs, Carsten; Freed, Jack H.; Hoffman, Brian M.; Lin, Hening [Journal of the American Chemical Society, 2016, vol. 138, # 31, p. 9755 - 9758]
  • 42
  • C11H16INO [ No CAS ]
  • [ 2457-80-9 ]
  • C22H31N6O4S(1+)*ClO4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With silver perchlorate In formic acid; acetic acid at 0 - 20℃; for 2.33h;
Reference： [1]Dong, Min; Horitani, Masaki; Dzikovski, Boris; Freed, Jack H.; Ealick, Steven E.; Hoffman, Brian M.; Lin, Hening [Journal of the American Chemical Society, 2017, vol. 139, # 16, p. 5680 - 5683]
  • 43
  • [ 20549-68-2 ]
  • [ 2457-80-9 ]
  • C20H26N5O4S(1+)*ClO4(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With silver perchlorate In formic acid; acetic acid at 0 - 20℃; for 2.33h;
Reference： [1]Dong, Min; Horitani, Masaki; Dzikovski, Boris; Freed, Jack H.; Ealick, Steven E.; Hoffman, Brian M.; Lin, Hening [Journal of the American Chemical Society, 2017, vol. 139, # 16, p. 5680 - 5683]
  • 44
  • [ 2457-80-9 ]
  • [ 167479-01-8 ]
  • C19H31N6O5S(1+)*ClO4(1-) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 5680 - 5683
  • 45
  • [ 6092-54-2 ]
  • [ 2457-80-9 ]
  • N-(hexoxycarbonyl)-2′,3′-bis(hexylcarbonate)-5′-methylthioadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 5'-Deoxy-5'-methylthioadenosine With 1-methyl-1H-imidazole In dichloromethane at 0℃; for 0.0833333h; Stage #2: n-hexyl chloroformate In dichloromethane at 0 - 20℃; for 72h; General procedure for the synthesis of N-(alkyloxy)carbonyl-MTA prodrugs (2a-f) General procedure: 5′-MTA was suspended in 10-20 ml anhydrous dichloromethane.1-Methylimidazole (8 eq.) was added and thesuspension was stirred at 0 °C for 5 mins. An alkyl chloroformate(6 eq.) was added dropwise to the cold suspensionover 5 mins while maintaining the temperature at 0 °C. Thereaction mixture was allowed to warm to room temperatureand was stirred for an additional 3 days. The reaction progresswas monitored using TLC and LCMS. The reactionmixture was diluted with dichloromethane (20 mL) andwashed successively twice each with saturated NaHCO3(10 ml) and brine (10 mL). The organic phase was separatedand dried over Na2SO4 and filtered. The solvent was evaporated,and the crude product was purified by column chromatography using methanol and dichloromethane as aneluent to give the intermediate 3a-f as an oil. To a solution of intermediate 3a-f in 5 mL ethanol wasadded 0.1 N NaOH (1 eq.) and the resulting reaction mixturewas stirred at room temperature for 12 h. On completionof the reaction, 1 N HCl was added to the reactionmixture until the pH was neutral. Dichloromethane (10 mL)was then added to the reaction mixture followed by washingwith brine (5 mL). The organic layer was dried overNa2SO4, filtered and the solvent was evaporated. The crudeproduct was purified using column chromatography inmethanol in dichloromethane to give final target compounds2a-f as white solids. N-(hexoxycarbonyl)-2′,3′-bis(hexylcarbonate)-MTA(3a): Yield, 140 mg (61%) obtained from 100 mg(0.336 mmol) of MTA. 1H NMR (400MHz, Methanol-d4) δ(ppm): 8.64 (s, 1H), 8.50 (s, 1H), 6.34 (d, J = 5.3 Hz, 1H),6.09 (t, J = 5.5 Hz, 1H), 5.64 (dd, J = 5.7, 4.7 Hz, 1H), 4.46(td, J = 5.9, 4.6 Hz, 1H), 4.26 (t, J = 6.7 Hz, 2H), 4.23-4.01(m, 4H), 3.11-2.90 (m, 2H), 2.11 (s, 3H), 1.81-1.65 (m,4H), 1.60 (dq, J = 8.0, 6.5 Hz, 2H), 1.51-1.23 (m, 18H),0.98-0.87 (m, 9H); 13C NMR (100 MHz, Methanol-d4) δ(ppm): 154.2, 153.9, 152.2, 152.1, 151.1, 150.0, 142.9,122.4, 86.3, 81.8, 75.5, 75.4, 68.8, 68.6, 65.7, 35.5, 33.4,31.3, 31.2, 31.2, 30.9, 28.5, 28.3, 28.2, 27.9, 25.4, 25.3,25.1, 25.0, 24.7, 22.3, 22.3, 22.2, 22.1, 15.2, 13.1, 13.1,13.0; LCMS (ESI+): 682.3 [M+H]+.
Reference： [1]Ranade, Ashwini Sadanand; Bertino, Joseph R.; Hu, Longqin [Medicinal Chemistry Research, 2021, vol. 30, # 7, p. 1358 - 1365]
  • 46
  • [ 2457-80-9 ]
  • [ 592-34-7 ]
  • N-(butoxycarbonyl)-2′,3′-bis(butylcarbonate)-5′-methylthioadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 5'-Deoxy-5'-methylthioadenosine With 1-methyl-1H-imidazole In dichloromethane at 0℃; for 0.0833333h; Stage #2: carbonochloridic acid, butyl ester In dichloromethane at 0 - 20℃; for 72h; General procedure for the synthesis of N-(alkyloxy)carbonyl-MTA prodrugs (2a-f) General procedure: 5′-MTA was suspended in 10-20 ml anhydrous dichloromethane.1-Methylimidazole (8 eq.) was added and thesuspension was stirred at 0 °C for 5 mins. An alkyl chloroformate(6 eq.) was added dropwise to the cold suspensionover 5 mins while maintaining the temperature at 0 °C. Thereaction mixture was allowed to warm to room temperatureand was stirred for an additional 3 days. The reaction progresswas monitored using TLC and LCMS. The reactionmixture was diluted with dichloromethane (20 mL) andwashed successively twice each with saturated NaHCO3(10 ml) and brine (10 mL). The organic phase was separatedand dried over Na2SO4 and filtered. The solvent was evaporated,and the crude product was purified by column chromatography using methanol and dichloromethane as aneluent to give the intermediate 3a-f as an oil. To a solution of intermediate 3a-f in 5 mL ethanol wasadded 0.1 N NaOH (1 eq.) and the resulting reaction mixturewas stirred at room temperature for 12 h. On completionof the reaction, 1 N HCl was added to the reactionmixture until the pH was neutral. Dichloromethane (10 mL)was then added to the reaction mixture followed by washingwith brine (5 mL). The organic layer was dried overNa2SO4, filtered and the solvent was evaporated. The crudeproduct was purified using column chromatography inmethanol in dichloromethane to give final target compounds2a-f as white solids.
Reference： [1]Ranade, Ashwini Sadanand; Bertino, Joseph R.; Hu, Longqin [Medicinal Chemistry Research, 2021, vol. 30, # 7, p. 1358 - 1365]
  • 47
  • [ 2457-80-9 ]
  • [ 108-23-6 ]
  • N-(isopropoxycarbonyl)-2′,3′-bis(isopropylcarbonate)-5′-methylthioadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% Stage #1: 5'-Deoxy-5'-methylthioadenosine With 1-methyl-1H-imidazole In dichloromethane at 0℃; for 0.0833333h; Stage #2: isopropyl chloroformate In dichloromethane at 0 - 20℃; for 72h; General procedure for the synthesis of N-(alkyloxy)carbonyl-MTA prodrugs (2a-f) General procedure: 5′-MTA was suspended in 10-20 ml anhydrous dichloromethane.1-Methylimidazole (8 eq.) was added and thesuspension was stirred at 0 °C for 5 mins. An alkyl chloroformate(6 eq.) was added dropwise to the cold suspensionover 5 mins while maintaining the temperature at 0 °C. Thereaction mixture was allowed to warm to room temperatureand was stirred for an additional 3 days. The reaction progresswas monitored using TLC and LCMS. The reactionmixture was diluted with dichloromethane (20 mL) andwashed successively twice each with saturated NaHCO3(10 ml) and brine (10 mL). The organic phase was separatedand dried over Na2SO4 and filtered. The solvent was evaporated,and the crude product was purified by column chromatography using methanol and dichloromethane as aneluent to give the intermediate 3a-f as an oil. To a solution of intermediate 3a-f in 5 mL ethanol wasadded 0.1 N NaOH (1 eq.) and the resulting reaction mixturewas stirred at room temperature for 12 h. On completionof the reaction, 1 N HCl was added to the reactionmixture until the pH was neutral. Dichloromethane (10 mL)was then added to the reaction mixture followed by washingwith brine (5 mL). The organic layer was dried overNa2SO4, filtered and the solvent was evaporated. The crudeproduct was purified using column chromatography inmethanol in dichloromethane to give final target compounds2a-f as white solids.
Reference： [1]Ranade, Ashwini Sadanand; Bertino, Joseph R.; Hu, Longqin [Medicinal Chemistry Research, 2021, vol. 30, # 7, p. 1358 - 1365]
  • 48
  • [ 541-41-3 ]
  • [ 2457-80-9 ]
  • N-(ethoxycarbonyl)-2′,3′-bis(ethylcarbonate)-5′-methylthioadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% Stage #1: 5'-Deoxy-5'-methylthioadenosine With 1-methyl-1H-imidazole In dichloromethane at 0℃; for 0.0833333h; Stage #2: chloroformic acid ethyl ester In dichloromethane at 0 - 20℃; for 72h; General procedure for the synthesis of N-(alkyloxy)carbonyl-MTA prodrugs (2a-f) General procedure: 5′-MTA was suspended in 10-20 ml anhydrous dichloromethane.1-Methylimidazole (8 eq.) was added and thesuspension was stirred at 0 °C for 5 mins. An alkyl chloroformate(6 eq.) was added dropwise to the cold suspensionover 5 mins while maintaining the temperature at 0 °C. Thereaction mixture was allowed to warm to room temperatureand was stirred for an additional 3 days. The reaction progresswas monitored using TLC and LCMS. The reactionmixture was diluted with dichloromethane (20 mL) andwashed successively twice each with saturated NaHCO3(10 ml) and brine (10 mL). The organic phase was separatedand dried over Na2SO4 and filtered. The solvent was evaporated,and the crude product was purified by column chromatography using methanol and dichloromethane as aneluent to give the intermediate 3a-f as an oil. To a solution of intermediate 3a-f in 5 mL ethanol wasadded 0.1 N NaOH (1 eq.) and the resulting reaction mixturewas stirred at room temperature for 12 h. On completionof the reaction, 1 N HCl was added to the reactionmixture until the pH was neutral. Dichloromethane (10 mL)was then added to the reaction mixture followed by washingwith brine (5 mL). The organic layer was dried overNa2SO4, filtered and the solvent was evaporated. The crudeproduct was purified using column chromatography inmethanol in dichloromethane to give final target compounds2a-f as white solids.
Reference： [1]Ranade, Ashwini Sadanand; Bertino, Joseph R.; Hu, Longqin [Medicinal Chemistry Research, 2021, vol. 30, # 7, p. 1358 - 1365]
  • 49
  • [ 2457-80-9 ]
  • [ 109-61-5 ]
  • N-(propoxycarbonyl)-2′,3′-bis(propylcarbonate)-5′-methylthioadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% Stage #1: 5'-Deoxy-5'-methylthioadenosine With 1-methyl-1H-imidazole In dichloromethane at 0℃; for 0.0833333h; Stage #2: propoxycarbonyl chloride In dichloromethane at 0 - 20℃; for 72h; General procedure for the synthesis of N-(alkyloxy)carbonyl-MTA prodrugs (2a-f) General procedure: 5′-MTA was suspended in 10-20 ml anhydrous dichloromethane.1-Methylimidazole (8 eq.) was added and thesuspension was stirred at 0 °C for 5 mins. An alkyl chloroformate(6 eq.) was added dropwise to the cold suspensionover 5 mins while maintaining the temperature at 0 °C. Thereaction mixture was allowed to warm to room temperatureand was stirred for an additional 3 days. The reaction progresswas monitored using TLC and LCMS. The reactionmixture was diluted with dichloromethane (20 mL) andwashed successively twice each with saturated NaHCO3(10 ml) and brine (10 mL). The organic phase was separatedand dried over Na2SO4 and filtered. The solvent was evaporated,and the crude product was purified by column chromatography using methanol and dichloromethane as aneluent to give the intermediate 3a-f as an oil. To a solution of intermediate 3a-f in 5 mL ethanol wasadded 0.1 N NaOH (1 eq.) and the resulting reaction mixturewas stirred at room temperature for 12 h. On completionof the reaction, 1 N HCl was added to the reactionmixture until the pH was neutral. Dichloromethane (10 mL)was then added to the reaction mixture followed by washingwith brine (5 mL). The organic layer was dried overNa2SO4, filtered and the solvent was evaporated. The crudeproduct was purified using column chromatography inmethanol in dichloromethane to give final target compounds2a-f as white solids.
Reference： [1]Ranade, Ashwini Sadanand; Bertino, Joseph R.; Hu, Longqin [Medicinal Chemistry Research, 2021, vol. 30, # 7, p. 1358 - 1365]
  • 50
  • [ 628-12-6 ]
  • [ 2457-80-9 ]
  • N-(2-methoxyethyoxy)carbonyl-2′,3′-bis(2-methoxyethylcarbonate)-5′-methylthioadenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: 5'-Deoxy-5'-methylthioadenosine With 1-methyl-1H-imidazole In dichloromethane at 0℃; for 0.0833333h; Stage #2: 2-Methoxyethyl chloroformate In dichloromethane at 0 - 20℃; for 72h; General procedure for the synthesis of N-(alkyloxy)carbonyl-MTA prodrugs (2a-f) General procedure: 5′-MTA was suspended in 10-20 ml anhydrous dichloromethane.1-Methylimidazole (8 eq.) was added and thesuspension was stirred at 0 °C for 5 mins. An alkyl chloroformate(6 eq.) was added dropwise to the cold suspensionover 5 mins while maintaining the temperature at 0 °C. Thereaction mixture was allowed to warm to room temperatureand was stirred for an additional 3 days. The reaction progresswas monitored using TLC and LCMS. The reactionmixture was diluted with dichloromethane (20 mL) andwashed successively twice each with saturated NaHCO3(10 ml) and brine (10 mL). The organic phase was separatedand dried over Na2SO4 and filtered. The solvent was evaporated,and the crude product was purified by column chromatography using methanol and dichloromethane as aneluent to give the intermediate 3a-f as an oil. To a solution of intermediate 3a-f in 5 mL ethanol wasadded 0.1 N NaOH (1 eq.) and the resulting reaction mixturewas stirred at room temperature for 12 h. On completionof the reaction, 1 N HCl was added to the reactionmixture until the pH was neutral. Dichloromethane (10 mL)was then added to the reaction mixture followed by washingwith brine (5 mL). The organic layer was dried overNa2SO4, filtered and the solvent was evaporated. The crudeproduct was purified using column chromatography inmethanol in dichloromethane to give final target compounds2a-f as white solids.
Reference： [1]Ranade, Ashwini Sadanand; Bertino, Joseph R.; Hu, Longqin [Medicinal Chemistry Research, 2021, vol. 30, # 7, p. 1358 - 1365]

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