Alternatived Products of [ 153631-19-7 ]
Product Details of [ 153631-19-7 ]
CAS No. : 153631-19-7
MDL No. : MFCD01631071
Formula :
C32 H34 N2 O8
Boiling Point :
-
Linear Structure Formula : -
InChI Key : VFLOXJCZWDDILQ-NODMTMHWSA-N
M.W :
574.62
Pubchem ID : 10438068
Synonyms :
Calculated chemistry of [ 153631-19-7 ]
Physicochemical Properties
Num. heavy atoms :
42
Num. arom. heavy atoms :
24
Fraction Csp3 :
0.31
Num. rotatable bonds :
10
Num. H-bond acceptors :
8.0
Num. H-bond donors :
2.0
Molar Refractivity :
155.02
TPSA :
121.24 Ų
Pharmacokinetics
GI absorption :
High
BBB permeant :
No
P-gp substrate :
Yes
CYP1A2 inhibitor :
No
CYP2C19 inhibitor :
No
CYP2C9 inhibitor :
Yes
CYP2D6 inhibitor :
Yes
CYP3A4 inhibitor :
Yes
Log Kp (skin permeation) :
-7.53 cm/s
Lipophilicity
Log Po/w (iLOGP) :
4.23
Log Po/w (XLOGP3) :
3.21
Log Po/w (WLOGP) :
2.71
Log Po/w (MLOGP) :
1.38
Log Po/w (SILICOS-IT) :
4.25
Consensus Log Po/w :
3.15
Druglikeness
Lipinski :
1.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
0.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-5.19
Solubility :
0.00373 mg/ml ; 0.00000649 mol/l
Class :
Moderately soluble
Log S (Ali) :
-5.43
Solubility :
0.00214 mg/ml ; 0.00000373 mol/l
Class :
Moderately soluble
Log S (SILICOS-IT) :
-8.24
Solubility :
0.00000331 mg/ml ; 0.0000000057 mol/l
Class :
Poorly soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
0.0 alert
Leadlikeness :
2.0
Synthetic accessibility :
5.57
Safety of [ 153631-19-7 ]
Application In Synthesis of [ 153631-19-7 ]
* 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 [ 153631-19-7 ]
1
[ 124482-92-4 ]
[ 153631-19-7 ]
[ 168611-18-5 ]
Yield Reaction Conditions Operation in experiment
75%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 4.5h;
2
[ 153631-19-7 ]
[ 55486-09-4 ]
3
[ 153631-18-6 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
71%
With potassium <i>tert</i>-butylate In dichloromethane for 1.5h; Ambient temperature;
4
[ 40615-36-9 ]
[ 55486-09-4 ]
[ 153631-19-7 ]
Reference:
[1]ChemBioChem,2017,vol. 18,p. 2236 - 2241
[2]Organic and Biomolecular Chemistry,2016,vol. 14,p. 4927 - 4942
[3]Helvetica Chimica Acta,1995,vol. 78,p. 486 - 504
[4]Nucleosides and Nucleotides,1997,vol. 16,p. 1629 - 1632
5
[ 102691-36-1 ]
[ 153631-19-7 ]
[ 168611-18-5 ]
Yield Reaction Conditions Operation in experiment
96%
With N,N-diisopropylamine tetrazolide In dichloromethane Ambient temperature;
6
[ 153631-19-7 ]
3-tert-butylphenyl chlorothionoformate
[ No CAS ]
[ 199581-44-7 ]
Yield Reaction Conditions Operation in experiment
With dmap In dichloromethane at 0 - 20℃; for 18h; Yield given;
7
[ 108-24-7 ]
[ 153631-19-7 ]
Acetic acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
100%
With pyridine at 20℃;
With pyridine at 20℃;
Reference:
[1]Jana, Sunit K.; Leonard, Peter; Ingale, Sachin A.; Seela, Frank
[Organic and Biomolecular Chemistry, 2016, vol. 14, # 21, p. 4927 - 4942]
[2]Ostrowski, Tomasz; Maurizot, Jean-Claude; Adeline, Marie-Therese; Fourrey, Jean-Louis; Clivio, Pascale
[Journal of Organic Chemistry, 2003, vol. 68, # 17, p. 6502 - 6510]
8
magnesium methanolate
[ No CAS ]
[ 817623-11-3 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
In N,N-dimethyl-formamide at 100℃; for 2.5h;
9
[ 937-63-3 ]
[ 153631-19-7 ]
[ 719302-94-0 ]
Yield Reaction Conditions Operation in experiment
86%
With dmap In acetonitrile at 20℃;
10
[ 153631-19-7 ]
1-{(2R,3R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-methoxy-tetrahydro-furan-2-yl}-5-methyl-1H-pyrimidine-2,4-dione
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 86 percent / (N,N-dimethylamino)pyridine / acetonitrile / 20 °C
2: 10 percent / AIBN / benzene / Heating
11
[ 153631-19-7 ]
[ 200067-01-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1.1: 86 percent / (N,N-dimethylamino)pyridine / acetonitrile / 20 °C
2.1: 45 percent / AIBN / benzene / Heating
3.1: NaIO4 ; OsO4 / H2 O / 5 h / 20 °C
4.1: acetic acid / CH2 Cl2 ; toluene / 35 °C / atmospheric pressure
5.1: 0.54 g / Cl3 CCO2 H / CH2 Cl2 / 0.17 h / 20 °C
6.1: sodium cyanoborohydride; glacial acetic acid / 1.25 h / 5 - 20 °C
6.2: sodium cyanoborohydride / H2 O / 1.25 h / 5 - 20 °C
7.1: 0.26 g / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C
12
[ 153631-19-7 ]
[ 719303-08-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 86 percent / (N,N-dimethylamino)pyridine / acetonitrile / 20 °C
2: 45 percent / AIBN / benzene / Heating
3: NaIO4 ; OsO4 / H2 O / 5 h / 20 °C
4: acetic acid / CH2 Cl2 ; toluene / 35 °C / atmospheric pressure
5: 0.17 g / Cl3 CCO2 H / CH2 Cl2 / 0.17 h / 20 °C
13
[ 153631-19-7 ]
[ 719303-10-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 86 percent / (N,N-dimethylamino)pyridine / acetonitrile / 20 °C
2: 45 percent / AIBN / benzene / Heating
3: NaIO4 ; OsO4 / H2 O / 5 h / 20 °C
4: acetic acid / CH2 Cl2 ; toluene / 35 °C / atmospheric pressure
5: 0.54 g / Cl3 CCO2 H / CH2 Cl2 / 0.17 h / 20 °C
14
[ 153631-19-7 ]
C39 H50 FN5 O10 Si
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1.1: 86 percent / (N,N-dimethylamino)pyridine / acetonitrile / 20 °C
2.1: 45 percent / AIBN / benzene / Heating
3.1: NaIO4 ; OsO4 / H2 O / 5 h / 20 °C
4.1: acetic acid / CH2 Cl2 ; toluene / 35 °C / atmospheric pressure
5.1: 0.54 g / Cl3 CCO2 H / CH2 Cl2 / 0.17 h / 20 °C
6.1: sodium cyanoborohydride; glacial acetic acid / 1.25 h / 5 - 20 °C
6.2: sodium cyanoborohydride / H2 O / 1.25 h / 5 - 20 °C
15
[ 153631-19-7 ]
[ 719303-09-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1.1: 86 percent / (N,N-dimethylamino)pyridine / acetonitrile / 20 °C
2.1: 45 percent / AIBN / benzene / Heating
3.1: NaIO4 ; OsO4 / H2 O / 5 h / 20 °C
4.1: acetic acid / CH2 Cl2 ; toluene / 35 °C / atmospheric pressure
5.1: 0.17 g / Cl3 CCO2 H / CH2 Cl2 / 0.17 h / 20 °C
6.1: sodium cyanoborohydride; glacial acetic acid / 1.25 h / 5 - 20 °C
6.2: sodium cyanoborohydride / H2 O / 1.25 h / 5 - 20 °C
16
[ 153631-19-7 ]
[ 719302-99-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1.1: 86 percent / (N,N-dimethylamino)pyridine / acetonitrile / 20 °C
2.1: 45 percent / AIBN / benzene / Heating
3.1: NaIO4 ; OsO4 / H2 O / 5 h / 20 °C
4.1: acetic acid / CH2 Cl2 ; toluene / 35 °C / atmospheric pressure
5.1: 0.54 g / Cl3 CCO2 H / CH2 Cl2 / 0.17 h / 20 °C
6.1: sodium cyanoborohydride; glacial acetic acid / 1.25 h / 5 - 20 °C
6.2: sodium cyanoborohydride / H2 O / 1.25 h / 5 - 20 °C
7.1: 0.26 g / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C
8.1: 89 percent / (N,N-dimethylamino)pyridine; triethylamine; pyridine / CH2 Cl2 / 20 °C
17
[ 153631-19-7 ]
[ 198703-60-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 86 percent / (N,N-dimethylamino)pyridine / acetonitrile / 20 °C
2: 45 percent / AIBN / benzene / Heating
3: NaIO4 ; OsO4 / H2 O / 5 h / 20 °C
Multi-step reaction with 3 steps
1: DMAP / CH2 Cl2 / 18 h / 0 - 20 °C
2: 1,1'-azobis(cyclohexanecarbonitrile) / chlorobenzene / 80 - 100 °C
3: OsO4 , NaIO4 / H2 O; dioxane
Reference:
[1]Peoc'h, Didier; Swayze, Eric E.; Bhat, Balkrishen; Sanghvi, Yogesh S.
[Nucleosides, nucleotides and nucleic acids, 2004, vol. 23, # 1-2, p. 411 - 438]
[2]Dimock, Stuart; Bhat, Balkrishen; Peoc'h, Didier; Sanghvi, Yogesh S.; Swayze, Eric E.
[Nucleosides and Nucleotides, 1997, vol. 16, # 7-9, p. 1629 - 1632]
18
[ 153631-19-7 ]
[ 318246-97-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 86 percent / (N,N-dimethylamino)pyridine / acetonitrile / 20 °C
2: 45 percent / AIBN / benzene / Heating
Multi-step reaction with 2 steps
1: DMAP / CH2 Cl2 / 18 h / 0 - 20 °C
2: 1,1'-azobis(cyclohexanecarbonitrile) / chlorobenzene / 80 - 100 °C
Reference:
[1]Peoc'h, Didier; Swayze, Eric E.; Bhat, Balkrishen; Sanghvi, Yogesh S.
[Nucleosides, nucleotides and nucleic acids, 2004, vol. 23, # 1-2, p. 411 - 438]
[2]Dimock, Stuart; Bhat, Balkrishen; Peoc'h, Didier; Sanghvi, Yogesh S.; Swayze, Eric E.
[Nucleosides and Nucleotides, 1997, vol. 16, # 7-9, p. 1629 - 1632]
19
[ 22423-26-3 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: pyridine; DMAP / 20 °C
2: dimethylformamide / 2.5 h / 100 °C
20
[ 40615-36-9 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: pyridine; DMAP / 20 °C
2: dimethylformamide / 2.5 h / 100 °C
21
[ 153631-19-7 ]
[ 606972-27-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: pyridine / 20 °C
2: 93 mg / trifluoroacetic acid / CH2 Cl2 / 0.5 h / 20 °C
Multi-step reaction with 2 steps
1: pyridine / 20 °C
2: acetic acid / water / 20 °C
Reference:
[1]Ostrowski, Tomasz; Maurizot, Jean-Claude; Adeline, Marie-Therese; Fourrey, Jean-Louis; Clivio, Pascale
[Journal of Organic Chemistry, 2003, vol. 68, # 17, p. 6502 - 6510]
[2]Jana, Sunit K.; Leonard, Peter; Ingale, Sachin A.; Seela, Frank
[Organic and Biomolecular Chemistry, 2016, vol. 14, # 21, p. 4927 - 4942]
22
[ 153631-19-7 ]
[ 606972-26-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1.1: pyridine / 20 °C
2.1: 93 mg / trifluoroacetic acid / CH2 Cl2 / 0.5 h / 20 °C
3.1: tetrazole / acetonitrile / 0.5 h / 20 °C
4.1: iodine; 2,6-lutidine / acetonitrile; tetrahydrofuran; H2 O / 0.33 h / 20 °C
5.1: NH3 / methanol; H2 O / 20 °C
5.2: 8 mg / acetic acid / H2 O / 6 h / 20 °C
23
[ 153631-19-7 ]
C22 H31 N4 O14 P
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1.1: pyridine / 20 °C
2.1: 93 mg / trifluoroacetic acid / CH2 Cl2 / 0.5 h / 20 °C
3.1: tetrazole / acetonitrile / 0.5 h / 20 °C
4.1: iodine; 2,6-lutidine / acetonitrile; tetrahydrofuran; H2 O / 0.33 h / 20 °C
5.1: NH3 / methanol; H2 O / 20 °C
5.2: 8 mg / acetic acid / H2 O / 6 h / 20 °C
6.1: D2 O / 7.5 h / UV-irradiation
24
[ 153631-19-7 ]
C22 H31 N4 O14 P
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1.1: pyridine / 20 °C
2.1: 93 mg / trifluoroacetic acid / CH2 Cl2 / 0.5 h / 20 °C
3.1: tetrazole / acetonitrile / 0.5 h / 20 °C
4.1: iodine; 2,6-lutidine / acetonitrile; tetrahydrofuran; H2 O / 0.33 h / 20 °C
5.1: NH3 / methanol; H2 O / 20 °C
5.2: 8 mg / acetic acid / H2 O / 6 h / 20 °C
6.1: D2 O / 7.5 h / UV-irradiation
25
[ 153631-19-7 ]
C48 H54 N5 O16 P
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: pyridine / 20 °C
2: 93 mg / trifluoroacetic acid / CH2 Cl2 / 0.5 h / 20 °C
3: tetrazole / acetonitrile / 0.5 h / 20 °C
26
[ 153631-19-7 ]
[ 1055036-95-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: pyridine / 20 °C
2: 93 mg / trifluoroacetic acid / CH2 Cl2 / 0.5 h / 20 °C
3: tetrazole / acetonitrile / 0.5 h / 20 °C
4: iodine; 2,6-lutidine / acetonitrile; tetrahydrofuran; H2 O / 0.33 h / 20 °C
27
[ 153631-19-7 ]
3'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-3'-iodo-2'-O-methyl-5-methyluridine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 1.) pyridine / 1) CH2 Cl2 , -10 deg C, 0.75 h; 2) CH2 Cl2 , pyridine, -10 deg C, 2.5 h
2: Bu4 NI / toluene / 0.5 h / 80 °C
Reference:
[1]Bhat, Balkrishen; Swayze, Eric E.; Wheeler, Patrick; Dimock, Stuart; Perbost, Michel; Sanghvi, Yogesh S.
[Journal of Organic Chemistry, 1996, vol. 61, # 23, p. 8186 - 8199]
28
[ 50-69-1 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 11 steps
1: 1.) cc. H2 SO4 , 2.) NaH / 1.) 4 deg C, 16 h, 2.) DMF, 40 deg C
2: 125.9 g / SnCl4 / CH2 Cl2 / 35 h / 3 °C
3: pyridine, 4-(dimethylamino)-pyridine / 17 h
4: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe3 / 1.) ClCH2 CH2 Cl, reflux, 10 min, 2.) ClCH2 CH2 Cl, 70 deg C, 20 h
5: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h
6: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature
7: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C
8: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature
9: 30percent NaOMe / methanol / Ambient temperature; pH 11
10: 84 percent / H2 , NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr
11: pyridine / 5 h / Ambient temperature
29
[ 153631-19-7 ]
Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2-oxo-4-[1,2,4]triazol-1-yl-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 96 percent / diisopropylammonium-tetrazolide / CH2 Cl2 / Ambient temperature
2: 92 percent / Et3 N, POCl3 / acetonitrile / 16 h / Ambient temperature
30
[ 168427-35-8 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 9 steps
1: pyridine, 4-(dimethylamino)-pyridine / 17 h
2: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe3 / 1.) ClCH2 CH2 Cl, reflux, 10 min, 2.) ClCH2 CH2 Cl, 70 deg C, 20 h
3: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h
4: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature
5: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C
6: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature
7: 30percent NaOMe / methanol / Ambient temperature; pH 11
8: 84 percent / H2 , NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr
9: pyridine / 5 h / Ambient temperature
31
[ 163759-42-0 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 8 steps
1: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe3 / 1.) ClCH2 CH2 Cl, reflux, 10 min, 2.) ClCH2 CH2 Cl, 70 deg C, 20 h
2: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h
3: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature
4: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C
5: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature
6: 30percent NaOMe / methanol / Ambient temperature; pH 11
7: 84 percent / H2 , NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr
8: pyridine / 5 h / Ambient temperature
32
[ 163759-40-8 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 10 steps
1: 125.9 g / SnCl4 / CH2 Cl2 / 35 h / 3 °C
2: pyridine, 4-(dimethylamino)-pyridine / 17 h
3: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TfOSiMe3 / 1.) ClCH2 CH2 Cl, reflux, 10 min, 2.) ClCH2 CH2 Cl, 70 deg C, 20 h
4: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h
5: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature
6: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C
7: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature
8: 30percent NaOMe / methanol / Ambient temperature; pH 11
9: 84 percent / H2 , NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr
10: pyridine / 5 h / Ambient temperature
33
[ 168427-64-3 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 84 percent / H2 , NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr
2: pyridine / 5 h / Ambient temperature
34
1-[(2R,3R,4R,5R)-4-(2,4-Dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-methoxy-tetrahydro-furan-2-yl]-3-hydroxymethyl-5-methyl-1H-pyrimidine-2,4-dione
[ No CAS ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 30percent NaOMe / methanol / Ambient temperature; pH 11
2: 84 percent / H2 , NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr
3: pyridine / 5 h / Ambient temperature
35
[ 163759-43-1 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: 1,8-diazabicyclo<5.4.0>undec-7-ene / acetonitrile / 10 h
2: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature
3: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C
4: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature
5: 30percent NaOMe / methanol / Ambient temperature; pH 11
6: 84 percent / H2 , NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr
7: pyridine / 5 h / Ambient temperature
36
[ 163759-45-3 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C
2: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature
3: 30percent NaOMe / methanol / Ambient temperature; pH 11
4: 84 percent / H2 , NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr
5: pyridine / 5 h / Ambient temperature
37
[ 168427-40-5 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature
2: 30percent NaOMe / methanol / Ambient temperature; pH 11
3: 84 percent / H2 , NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr
4: pyridine / 5 h / Ambient temperature
38
[ 163759-44-2 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: 98 percent / 30percent NaOMe / methanol / 3 h / Ambient temperature
2: 98 percent / NaH / tetrahydrofuran / 40 - 70 °C
3: H2 / 5percent Pd/C / tetrahydrofuran / Ambient temperature
4: 30percent NaOMe / methanol / Ambient temperature; pH 11
5: 84 percent / H2 , NaOAc / 5percent Pd/C / methanol / 45 °C / 2250.2 Torr
6: pyridine / 5 h / Ambient temperature
39
[ 3180-76-5 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: 90 percent / NaOMe / methanol / 24 h / Ambient temperature
2: 71 percent / pyridine / 1.25 h / Ambient temperature
3: 65 percent / tetrabutylammonium hydroxide, pyridine / acetonitrile / 48 h / Heating
4: 1.) NaH / 1.) DMF, -40 deg C, 0.75 h, 2.) DMF, a) from -40 to -30 deg C, 0.75 h, b) RT, 4 h
5: 71 percent / potassium t-butoxide / CH2 Cl2 / 1.5 h / Ambient temperature
40
[ 65-71-4 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 7 steps
1: 1,1,1,3,3,3-hexamethyldisilazane, chlorotrimethyl silane / acetonitrile / 4 h / Heating
2: acetonitrile / 0.5 h / Heating
3: 90 percent / NaOMe / methanol / 24 h / Ambient temperature
4: 71 percent / pyridine / 1.25 h / Ambient temperature
5: 65 percent / tetrabutylammonium hydroxide, pyridine / acetonitrile / 48 h / Heating
6: 1.) NaH / 1.) DMF, -40 deg C, 0.75 h, 2.) DMF, a) from -40 to -30 deg C, 0.75 h, b) RT, 4 h
7: 71 percent / potassium t-butoxide / CH2 Cl2 / 1.5 h / Ambient temperature
41
[ 138239-62-0 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 65 percent / tetrabutylammonium hydroxide, pyridine / acetonitrile / 48 h / Heating
2: 1.) NaH / 1.) DMF, -40 deg C, 0.75 h, 2.) DMF, a) from -40 to -30 deg C, 0.75 h, b) RT, 4 h
3: 71 percent / potassium t-butoxide / CH2 Cl2 / 1.5 h / Ambient temperature
42
[ 153631-17-5 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 1.) NaH / 1.) DMF, -40 deg C, 0.75 h, 2.) DMF, a) from -40 to -30 deg C, 0.75 h, b) RT, 4 h
2: 71 percent / potassium t-butoxide / CH2 Cl2 / 1.5 h / Ambient temperature
43
[ 7288-28-0 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 6 steps
1: acetonitrile / 0.5 h / Heating
2: 90 percent / NaOMe / methanol / 24 h / Ambient temperature
3: 71 percent / pyridine / 1.25 h / Ambient temperature
4: 65 percent / tetrabutylammonium hydroxide, pyridine / acetonitrile / 48 h / Heating
5: 1.) NaH / 1.) DMF, -40 deg C, 0.75 h, 2.) DMF, a) from -40 to -30 deg C, 0.75 h, b) RT, 4 h
6: 71 percent / potassium t-butoxide / CH2 Cl2 / 1.5 h / Ambient temperature
44
[ 1463-10-1 ]
[ 153631-19-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 71 percent / pyridine / 1.25 h / Ambient temperature
2: 65 percent / tetrabutylammonium hydroxide, pyridine / acetonitrile / 48 h / Heating
3: 1.) NaH / 1.) DMF, -40 deg C, 0.75 h, 2.) DMF, a) from -40 to -30 deg C, 0.75 h, b) RT, 4 h
4: 71 percent / potassium t-butoxide / CH2 Cl2 / 1.5 h / Ambient temperature
45
[ 153631-19-7 ]
C28 H41 F3 N5 O11 P
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
2: dicyclohexyl-carbodiimide / dimethyl sulfoxide
3: dicyclohexyl-carbodiimide
4: pyridine
5: triethylamine tris(hydrogen fluoride)
Multi-step reaction with 5 steps
2: dicyclohexyl-carbodiimide / dimethyl sulfoxide
3: thionyl chloride
4: pyridine; 2,2-dimethoxy-propane
5: N-ethyl-N,N-diisopropylamine
46
[ 153631-19-7 ]
C28 H44 N5 O11 P
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
2: dicyclohexyl-carbodiimide / dimethyl sulfoxide
3: dicyclohexyl-carbodiimide
4: pyridine
5: triethylamine tris(hydrogen fluoride)
Multi-step reaction with 5 steps
2: dicyclohexyl-carbodiimide / dimethyl sulfoxide
3: thionyl chloride
4: pyridine / N,N-dimethyl-formamide
5: N-ethyl-N,N-diisopropylamine
47
[ 153631-19-7 ]
1-[3-O-acetyl-2-O-methyl-5-O-(p-toluenesulfonyl)-β-D-ribofuranosyl]uracil
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: pyridine / 20 °C
2: acetic acid / water / 20 °C
3: pyridine; p-toluenesulfonyl chloride / 12 h / 20 °C
48
[ 153631-19-7 ]
3'-O-acetyl-2,5'-anhydro-2'-O-5-dimethyluridine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: pyridine / 20 °C
2: acetic acid / water / 20 °C
3: pyridine; p-toluenesulfonyl chloride / 12 h / 20 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / Reflux
49
[ 153631-19-7 ]
2,5'-anhydro-2'-O-methyl-5-methyluridine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 5 steps
1: pyridine / 20 °C
2: acetic acid / water / 20 °C
3: pyridine; p-toluenesulfonyl chloride / 12 h / 20 °C
4: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / Reflux
5: potassium carbonate / methanol / 0.33 h
50
[ 18162-48-6 ]
[ 153631-19-7 ]
C38 H48 N2 O8 Si
[ No CAS ]
Yield Reaction Conditions Operation in experiment
83%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;