CAS No.964-21-6,O6-METHYL-2'-DEOXYGUANOSINE Suppliers

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Zibo Hangyu Biotechnology Development Co., Ltd

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Synthetic route

: 82921-45-7
2'-deoxy-N2-isobutyryl-O6-methylguanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
With ammonium hydroxide at 50℃; for 72h;	100%
With potassium hydroxide for 8h; Ambient temperature;	99%
With potassium hydroxide at 22℃; Rate constant;

: 128790-76-1
2-N-trifluoroacetamido-6-pentafluorophenoxy-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine

: 124-41-4
sodium methylate

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
In methanol at 55℃; for 36h;	85%

: 2-amino-9-[2-deoxy-3,5-di-O-(4-toluoyl)-β-D-erythto-pentofuranosyl]-6-methoxy-9-H-purine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
With sodium methylate In methanol for 1h;	76%

: 124-41-4
sodium methylate

: 69992-11-6
2-amino-6-chloro-9-[(3’,5’-di-O-acetyl-2’-deoxy)-β-D-ribofuranosyl]purine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
In methanol at 0 - 20℃; for 6h; Inert atmosphere;	69%

: 142738-49-6
(2R,3S,5R)-5-(2-Amino-6-methoxy-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-ol

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 0.166667h;	54%

: 705255-09-0
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-(imidazol-1-yl)purine

: 67-56-1
methanol

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
With Dowex 1 x 2 (OH-) resin at 20℃;	52%

: 17287-03-5
trimethylsulphonium hydroxide

: 961-07-9
2'-Deoxyguanosine

A: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

B: 5132-79-6
N1-methyl-2'-deoxyguanosine

C: 107149-64-4
2'-deoxy-7-methylguanosine

D: 76551-24-1
9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-1-methyl-2-methylamino-1,9-dihydro-purin-6-one

Conditions

Conditions	Yield
In methanol; N,N-dimethyl-formamide at 70℃; for 1h; Further byproducts given;	A 6 mg B 23% C n/a D 7 mg
In methanol; N,N-dimethyl-formamide at 70℃; for 1h; Further byproducts given;	A 6 mg B 19 mg C n/a D 7 mg

...Expand

: 124-41-4
sodium methylate

: 961-07-9
2'-Deoxyguanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
With pyridine; trifluoroacetic anhydride 1. ice bath, 10 min, 2. methanol, 24 h; Yield given. Multistep reaction;

: 684-93-5
1-methyl-1-nitrosourea

: 961-07-9
2'-Deoxyguanosine

A: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

B: 5132-79-6
N1-methyl-2'-deoxyguanosine

C: 812-00-0
methylphosphate

D: 813-78-5
dimethylphosphoric acid

E: 578-76-7
7-methylguanine

F: 28074-91-1
N7-Me-dGuo

Conditions

Conditions	Yield
With sodium hydroxide; phosphate buffer In methanol; water at 37℃; Product distribution; various pH values;

...Expand

: 302584-95-8
N2-phenylacetyl-O6-methoxycarbonylmethyl-2'-deoxyguanosine

A: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

B: 189457-83-8
[2-Amino-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yloxy]-acetic acid methyl ester

C: O6-carboxymethyl-2'-deoxyguanosine

D: N2-phenylacetyl-O6-carboxymethyl-2'-deoxyguanosine

Conditions

Conditions	Yield
With potassium carbonate In methanol at 20℃; Product distribution; Further Variations:; Reagents; Hydrolysis;

...Expand

: 302584-95-8
N2-phenylacetyl-O6-methoxycarbonylmethyl-2'-deoxyguanosine

A: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

B: O6-carboxymethyl-2'-deoxyguanosine

C: N2-phenylacetyl-O6-methyl-2'-deoxyguanosine

D: N2-phenylacetyl-O6-carboxymethyl-2'-deoxyguanosine

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; Product distribution; Further Variations:; Reagents; Hydrolysis;

...Expand

: 66-27-3
Methyl methanesulfonate

calf thymus DNA: calf thymus DNA

A: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

B: 578-76-7
7-methylguanine

C: 60192-57-6
3-methyladenine

Conditions

Conditions	Yield
In various solvent(s) at 20℃; for 24h; pH=7.8; Methylation;

...Expand

calf thymus DNA: calf thymus DNA

: methyl 3-((1-methyl-5-((1-methyl-5-(propylcarbamoyl)-1H-pyrrol-3-yl)carbamoyl)-1H-pyrrol-3-yl)amino)-3-oxopropane-1-sulfonate

A: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

B: 578-76-7
7-methylguanine

C: 60192-57-6
3-methyladenine

Conditions

Conditions	Yield
In various solvent(s) at 20℃; for 24h; pH=8.0; Methylation;

...Expand

: 705255-08-9
2-amino-9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-(imidazol-1-yl)purine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 407 mg / NH3 / methanol / 3 h / 70 °C 2: 52 percent / Dowex 1 x 2 (OH-) resin / 20 °C View Scheme

: 705255-07-8
3',5'-di-O-acetyl-2'-deoxy-2-N-(mono-p-methoxytrityl)guanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Ph3P; I2; EtN(iPr)2 / toluene / 2 h / 80 °C 2: 813 mg / AcOH; H2O / dioxane / 3 h / 55 °C 3: 407 mg / NH3 / methanol / 3 h / 70 °C 4: 52 percent / Dowex 1 x 2 (OH-) resin / 20 °C View Scheme

: Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(6-imidazol-1-yl-2-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-purin-9-yl)-tetrahydro-furan-3-yl ester

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 813 mg / AcOH; H2O / dioxane / 3 h / 55 °C 2: 407 mg / NH3 / methanol / 3 h / 70 °C 3: 52 percent / Dowex 1 x 2 (OH-) resin / 20 °C View Scheme

: 105821-12-3
3',5'-di-O-acetyl-2'-deoxy-2-N-(di-p-methoxytrityl)guanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Ph3P; I2; EtN(iPr)2 / toluene / 2 h / 80 °C 2: AcOH; H2O / dioxane / 20 °C 3: 407 mg / NH3 / methanol / 3 h / 70 °C 4: 52 percent / Dowex 1 x 2 (OH-) resin / 20 °C View Scheme

: Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-(2-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-6-imidazol-1-yl-purin-9-yl)-tetrahydro-furan-3-yl ester

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: AcOH; H2O / dioxane / 20 °C 2: 407 mg / NH3 / methanol / 3 h / 70 °C 3: 52 percent / Dowex 1 x 2 (OH-) resin / 20 °C View Scheme

: 69992-10-5
3',5'-di-O-acetyl-2'-deoxyguanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / pyridine; EtN(iPr)2 / 20 °C 2: Ph3P; I2; EtN(iPr)2 / toluene / 2 h / 80 °C 3: AcOH; H2O / dioxane / 20 °C 4: 407 mg / NH3 / methanol / 3 h / 70 °C 5: 52 percent / Dowex 1 x 2 (OH-) resin / 20 °C View Scheme
Multi-step reaction with 5 steps 1: 97 percent / pyridine; EtN(iPr)2 / 15 h / 20 °C 2: Ph3P; I2; EtN(iPr)2 / toluene / 2 h / 80 °C 3: 813 mg / AcOH; H2O / dioxane / 3 h / 55 °C 4: 407 mg / NH3 / methanol / 3 h / 70 °C 5: 52 percent / Dowex 1 x 2 (OH-) resin / 20 °C View Scheme
Multi-step reaction with 2 steps 1: N-benzyl-N,N,N-triethylammonium chloride; N,N-dimethyl-aniline; trichlorophosphate / acetonitrile / 1.17 h / 0 °C / Inert atmosphere; Reflux 2: methanol / 6 h / 0 - 20 °C / Inert atmosphere View Scheme

: 4330-21-6
2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / powdered KOH, tris<2-(2-methoxy-ethoxy)ethyl>amine / acetonitrile / 0.25 h 2: 76 percent / 0.1M NaOMe / methanol / 1 h View Scheme

: 20535-83-5
O-methylguanine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / powdered KOH, tris<2-(2-methoxy-ethoxy)ethyl>amine / acetonitrile / 0.25 h 2: 76 percent / 0.1M NaOMe / methanol / 1 h View Scheme

: 82921-43-5
2-N-3',5'-O-triisobutyryl-6-O-(2,4,6-triisopropylbenzenesulfonyl)-2'-deoxyguanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Me3N, 2.) 1,8-diazabicyclo<5.4.0>undecene, 3.) NaOH 2: KOH-methanol / 22 °C View Scheme
Multi-step reaction with 3 steps 1: CH2Cl2 / 0.17 h / 0 °C 2: 1.) DBU 2.) 1N NaOH / 0.17 h / 0 °C 3: 100 percent / NH4OH / 72 h / 50 °C View Scheme

: 81144-43-6
5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: N-methylimidazole (NMI) / pyridine / 0.5 h / 20 °C 2: 81 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 16 h 3: 71 percent / N-methylpyrrolidine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 20 h / 20 °C 4: 85 percent / NH3 / methanol / 16 h / 0 - 5 °C 5: 54 percent / TFA / CH2Cl2 / 0.17 h View Scheme

: 91592-76-6
5'-O-(4,4'-dimethoxytrityl)-2-N-(diphenylacetyl)-2'-deoxyguanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: conc. NH4OH / dioxane / 24 h / 50 °C 2: N-methylimidazole (NMI) / pyridine / 0.5 h / 20 °C 3: 81 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 16 h 4: 71 percent / N-methylpyrrolidine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 20 h / 20 °C 5: 85 percent / NH3 / methanol / 16 h / 0 - 5 °C 6: 54 percent / TFA / CH2Cl2 / 0.17 h View Scheme

Yield

Multi-step reaction with 6 steps
1: conc. NH4OH / dioxane / 24 h / 50 °C
2: N-methylimidazole (NMI) / pyridine / 0.5 h / 20 °C
3: 81 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 16 h
4: 71 percent / N-methylpyrrolidine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 20 h / 20 °C
5: 85 percent / NH3 / methanol / 16 h / 0 - 5 °C
6: 54 percent / TFA / CH2Cl2 / 0.17 h
View Scheme

: 91288-93-6
2-N-diphenylacetyl-2'-deoxyguanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 88 percent / pyridine / 1 h / 20 °C 2: conc. NH4OH / dioxane / 24 h / 50 °C 3: N-methylimidazole (NMI) / pyridine / 0.5 h / 20 °C 4: 81 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 16 h 5: 71 percent / N-methylpyrrolidine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 20 h / 20 °C 6: 85 percent / NH3 / methanol / 16 h / 0 - 5 °C 7: 54 percent / TFA / CH2Cl2 / 0.17 h View Scheme

Yield

Multi-step reaction with 7 steps
1: 88 percent / pyridine / 1 h / 20 °C
2: conc. NH4OH / dioxane / 24 h / 50 °C
3: N-methylimidazole (NMI) / pyridine / 0.5 h / 20 °C
4: 81 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 16 h
5: 71 percent / N-methylpyrrolidine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 20 h / 20 °C
6: 85 percent / NH3 / methanol / 16 h / 0 - 5 °C
7: 54 percent / TFA / CH2Cl2 / 0.17 h
View Scheme

: 142738-45-2
3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-6-O-methyl-2'-deoxyguanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / NH3 / methanol / 16 h / 0 - 5 °C 2: 54 percent / TFA / CH2Cl2 / 0.17 h View Scheme

: 142738-43-0
3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyguanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 81 percent / 4-(dimethylamino)pyridine (DMAP), triethylamine / CH2Cl2 / 16 h 2: 71 percent / N-methylpyrrolidine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 20 h / 20 °C 3: 85 percent / NH3 / methanol / 16 h / 0 - 5 °C 4: 54 percent / TFA / CH2Cl2 / 0.17 h View Scheme

: 142738-44-1
3'-O-acetyl-5'-O-(4,4'-dimethoxytrityl)-6-O-<(2,4,6-triisopropylphenyl)sulfonyl>-2'-deoxyguanosine

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 71 percent / N-methylpyrrolidine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 20 h / 20 °C 2: 85 percent / NH3 / methanol / 16 h / 0 - 5 °C 3: 54 percent / TFA / CH2Cl2 / 0.17 h View Scheme

: 2,4,6-Triisopropyl-benzenesulfonate[2-isobutyrylamino-9-((2R,4S,5R)-4-isobutyryloxy-5-isobutyryloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-trimethyl-ammonium;

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) DBU 2.) 1N NaOH / 0.17 h / 0 °C 2: 100 percent / NH4OH / 72 h / 50 °C View Scheme

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

: 98-88-4
benzoyl chloride

: 80228-06-4
N2,O3,O5-tribenzoyl-O6-methyldeoxyguanosine

Conditions

Conditions	Yield
In pyridine 1.) 0 deg C, 0.5 h, 2.) room temperature, 2 h;	78%

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

: 97-72-3
2-Methylpropionic anhydride

: 82921-45-7
2'-deoxy-N2-isobutyryl-O6-methylguanosine

Conditions

Conditions	Yield
Stage #1: 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine With pyridine; chloro-trimethyl-silane at 20℃; for 4h; Stage #2: 2-Methylpropionic anhydride at 20℃; Stage #3: With ammonia In water at 0℃; for 0.25h;	69%

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

: 1256490-48-8
(S)-2-[(4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester

: isopropyl (2S)-2-{[((2‘-deoxy-O6-methylguanosine)-5'-yloxy)(phenoxy)phosphoryl]amino}propanoate

Conditions

Conditions	Yield
Stage #1: 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine With tert-butylmagnesium chloride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Stage #2: (S)-2-[(4-nitro-phenoxy)-phenoxy-phosphorylamino]propionic acid isopropyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 48h;	4%

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

: 80228-07-5
N2-benzoyl-O6-methyldeoxyguanosine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / pyridine / 1.) 0 deg C, 0.5 h, 2.) room temperature, 2 h 2: 77 percent / 2N NaOH / pyridine; ethanol / 0.08 h / Ambient temperature View Scheme

: 964-21-6
2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine

: 80228-08-6
N-benzoyl-5'-dimethoxytrityl-O6-methyldeoxyguanosine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent / pyridine / 1.) 0 deg C, 0.5 h, 2.) room temperature, 2 h 2: 77 percent / 2N NaOH / pyridine; ethanol / 0.08 h / Ambient temperature 3: 68 percent / pyridine / 18 h View Scheme

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