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443642-29-3

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443642-29-3 Usage

Uses

7-Deaza-2''-C-methyladenosine is a hepatitis C virus (HCV) polymerase inhibitor.

Check Digit Verification of cas no

The CAS Registry Mumber 443642-29-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 4,4,3,6,4 and 2 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 443642-29:
(8*4)+(7*4)+(6*3)+(5*6)+(4*4)+(3*2)+(2*2)+(1*9)=143
143 % 10 = 3
So 443642-29-3 is a valid CAS Registry Number.

443642-29-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (2R,3R,4R,5R)-2-(4-aminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)-3-methyloxolane-3,4-diol

1.2 Other means of identification

Product number -
Other names Lamevudine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:443642-29-3 SDS

443642-29-3Synthetic route

4-chloro-7-[2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine
443642-33-9

4-chloro-7-[2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
With ammonia at -78 - 85℃; for 24h;97%
With ammonia at -78 - 85℃; for 24h;97%
With ammonia In methanol at 85℃; for 14h;56%
4-phthalimido-7-[3',5'-di-O-(4-methylbenzoyl)-2'-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine
1053646-61-9

4-phthalimido-7-[3',5'-di-O-(4-methylbenzoyl)-2'-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
With N-butylamine In methanol; toluene at 64℃;25 g
4-amino-7H-pyrrolo[2,3-d]pyrimidine-2-sulfinic acid
1027082-25-2

4-amino-7H-pyrrolo[2,3-d]pyrimidine-2-sulfinic acid

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 84 percent / sulfuric acid / 5.5 h / 20 - 75 °C
2: 85.6 percent / N,N-dimethylacetamide; N,N-diisopropylethylamine
3: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
4: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
1,2:5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose

1,2:5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 10.81 kg / Triton X-405; KOH / toluene; H2O / 20 h / Heating
2.1: 9.02 kg / aq. sulfuric acid / toluene; acetonitrile / 19 °C
3.1: pyridine / acetonitrile / 12 h / 50 - 55 °C
4.1: aq. HBF4 / acetonitrile / 2 h / 50 - 55 °C
5.1: periodic acid / H2O / 0.5 h / 0 - 5 °C
5.2: diisopropylamine; aq. isopropyl acetate; aq. HCl / methanol / 0 °C
5.3: 4.03 kg / isopropyl acetate; H2 / Pd/C / 24 h / 50 °C / 2327.17 Torr
6.1: 93 percent / MsCl; Et3N / CH2Cl2 / 1.67 h / 30 °C
7.1: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
8.1: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
2-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)isoindoline-1,3-dione
741686-49-7

2-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)isoindoline-1,3-dione

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
2: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose

3-O-benzyl-1,2:5,6-di-O-isopropylidene-3-C-methyl-α-D-allofuranose

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 9.02 kg / aq. sulfuric acid / toluene; acetonitrile / 19 °C
2.1: pyridine / acetonitrile / 12 h / 50 - 55 °C
3.1: aq. HBF4 / acetonitrile / 2 h / 50 - 55 °C
4.1: periodic acid / H2O / 0.5 h / 0 - 5 °C
4.2: diisopropylamine; aq. isopropyl acetate; aq. HCl / methanol / 0 °C
4.3: 4.03 kg / isopropyl acetate; H2 / Pd/C / 24 h / 50 °C / 2327.17 Torr
5.1: 93 percent / MsCl; Et3N / CH2Cl2 / 1.67 h / 30 °C
6.1: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
7.1: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
1,2-anhydro-2-C-methyl-3,5-di-O-(4-methylbenzoyl)-α-D-ribofuranose
741686-50-0

1,2-anhydro-2-C-methyl-3,5-di-O-(4-methylbenzoyl)-α-D-ribofuranose

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
2: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
4-amino-7H-pyrrolo[2,3-d]pyrimidine hydrogen sulfate

4-amino-7H-pyrrolo[2,3-d]pyrimidine hydrogen sulfate

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85.6 percent / N,N-dimethylacetamide; N,N-diisopropylethylamine
2: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
3: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
2-C-methyl-3,5-di-O-(4-methylbenzoyl)-D-ribofuranose
943638-20-8

2-C-methyl-3,5-di-O-(4-methylbenzoyl)-D-ribofuranose

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 93 percent / MsCl; Et3N / CH2Cl2 / 1.67 h / 30 °C
2: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
3: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
C30H32O8

C30H32O8

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: periodic acid / H2O / 0.5 h / 0 - 5 °C
1.2: diisopropylamine; aq. isopropyl acetate; aq. HCl / methanol / 0 °C
1.3: 4.03 kg / isopropyl acetate; H2 / Pd/C / 24 h / 50 °C / 2327.17 Torr
2.1: 93 percent / MsCl; Et3N / CH2Cl2 / 1.67 h / 30 °C
3.1: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
4.1: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
C33H36O8

C33H36O8

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: aq. HBF4 / acetonitrile / 2 h / 50 - 55 °C
2.1: periodic acid / H2O / 0.5 h / 0 - 5 °C
2.2: diisopropylamine; aq. isopropyl acetate; aq. HCl / methanol / 0 °C
2.3: 4.03 kg / isopropyl acetate; H2 / Pd/C / 24 h / 50 °C / 2327.17 Torr
3.1: 93 percent / MsCl; Et3N / CH2Cl2 / 1.67 h / 30 °C
4.1: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
5.1: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
4,6-diamino-5-(2,2-diethoxyethyl)pyrimidine-2-thiol potassium salt

4,6-diamino-5-(2,2-diethoxyethyl)pyrimidine-2-thiol potassium salt

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 3.95 kg / aq. HCl / 50 °C
2: 99.1 percent / aq. KOH; hydrogen peroxide / 5 - 15 °C
3: 84 percent / sulfuric acid / 5.5 h / 20 - 75 °C
4: 85.6 percent / N,N-dimethylacetamide; N,N-diisopropylethylamine
5: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
6: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
3-O-benzyl-3-C-methyl-1,2-O-isopropylidene-α-D-allofuranose
55533-86-3, 120615-67-0

3-O-benzyl-3-C-methyl-1,2-O-isopropylidene-α-D-allofuranose

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: pyridine / acetonitrile / 12 h / 50 - 55 °C
2.1: aq. HBF4 / acetonitrile / 2 h / 50 - 55 °C
3.1: periodic acid / H2O / 0.5 h / 0 - 5 °C
3.2: diisopropylamine; aq. isopropyl acetate; aq. HCl / methanol / 0 °C
3.3: 4.03 kg / isopropyl acetate; H2 / Pd/C / 24 h / 50 °C / 2327.17 Torr
4.1: 93 percent / MsCl; Et3N / CH2Cl2 / 1.67 h / 30 °C
5.1: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
6.1: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
4-amino-7H-pyrrolo[2,3-d]pyrimidine-2-thiol
98198-24-4

4-amino-7H-pyrrolo[2,3-d]pyrimidine-2-thiol

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99.1 percent / aq. KOH; hydrogen peroxide / 5 - 15 °C
2: 84 percent / sulfuric acid / 5.5 h / 20 - 75 °C
3: 85.6 percent / N,N-dimethylacetamide; N,N-diisopropylethylamine
4: sodium hydride; N,N-dimethylacetamide / tetrahydrofuran; toluene / 9 h / 50 °C
5: 25 g / n-butylamine / methanol; toluene / 64 °C
View Scheme
(3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol
168427-35-8

(3R,4S,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxytetrahydrofuran-3-ol

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: Dess-Martin periodinane / CH2Cl2 / 72 h / 20 °C
2.1: 16.7 g / diethyl ether / 7 h / -30 - -15 °C
3.1: HBr; AcOH / CH2Cl2 / 4 h / 0 - 20 °C
4.1: NaH / acetonitrile / 4 h / 20 °C
4.2: 5.05 g / acetonitrile / 24 h / 20 °C
5.1: 66 percent / boron trichloride / CH2Cl2 / 5.5 h / -78 - -20 °C
6.1: 56 percent / NH3 / methanol / 14 h / 85 °C
View Scheme
Multi-step reaction with 5 steps
1.1: Dess-Martin periodane / dichloromethane / 73 h / 0 - 20 °C / Inert atmosphere
2.1: diethyl ether / 7 h / -55 - -15 °C
2.2: 0.5 h / 20 °C / Cooling with ice
3.1: hydrogen bromide; acetic acid / dichloromethane / 4 h / 0 - 20 °C
3.2: 24 h / 20 °C
4.1: boron trichloride / dichloromethane / 5.5 h / -78 - -20 °C
5.1: ammonia / methanol / 14 h / 85 °C / Autoclave
View Scheme
3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-erythro-pentafuranos-2-ulose
443642-30-6

3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-erythro-pentafuranos-2-ulose

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 16.7 g / diethyl ether / 7 h / -30 - -15 °C
2.1: HBr; AcOH / CH2Cl2 / 4 h / 0 - 20 °C
3.1: NaH / acetonitrile / 4 h / 20 °C
3.2: 5.05 g / acetonitrile / 24 h / 20 °C
4.1: 66 percent / boron trichloride / CH2Cl2 / 5.5 h / -78 - -20 °C
5.1: 56 percent / NH3 / methanol / 14 h / 85 °C
View Scheme
Multi-step reaction with 4 steps
1.1: diethyl ether / 7 h / -55 - -15 °C
1.2: 0.5 h / 20 °C / Cooling with ice
2.1: hydrogen bromide; acetic acid / dichloromethane / 4 h / 0 - 20 °C
2.2: 24 h / 20 °C
3.1: boron trichloride / dichloromethane / 5.5 h / -78 - -20 °C
4.1: ammonia / methanol / 14 h / 85 °C / Autoclave
View Scheme
(2S,3R,4R,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxy-3-methyltetrahydrofuran-3-ol
443642-31-7

(2S,3R,4R,5R)-4-((2,4-dichlorobenzyl)oxy)-5-(((2,4-dichlorobenzyl)oxy)methyl)-2-methoxy-3-methyltetrahydrofuran-3-ol

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: HBr; AcOH / CH2Cl2 / 4 h / 0 - 20 °C
2.1: NaH / acetonitrile / 4 h / 20 °C
2.2: 5.05 g / acetonitrile / 24 h / 20 °C
3.1: 66 percent / boron trichloride / CH2Cl2 / 5.5 h / -78 - -20 °C
4.1: 56 percent / NH3 / methanol / 14 h / 85 °C
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogen bromide; acetic acid / dichloromethane / 4 h / 0 - 20 °C
1.2: 24 h / 20 °C
2.1: boron trichloride / dichloromethane / 5.5 h / -78 - -20 °C
3.1: ammonia / methanol / 14 h / 85 °C / Autoclave
View Scheme
(3R,4R,5R)-2-Bromo-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-methyl-tetrahydro-furan-3-ol
847551-03-5

(3R,4R,5R)-2-Bromo-4-(2,4-dichloro-benzyloxy)-5-(2,4-dichloro-benzyloxymethyl)-3-methyl-tetrahydro-furan-3-ol

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: NaH / acetonitrile / 4 h / 20 °C
1.2: 5.05 g / acetonitrile / 24 h / 20 °C
2.1: 66 percent / boron trichloride / CH2Cl2 / 5.5 h / -78 - -20 °C
3.1: 56 percent / NH3 / methanol / 14 h / 85 °C
View Scheme
4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine
443642-32-8

4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 66 percent / boron trichloride / CH2Cl2 / 5.5 h / -78 - -20 °C
2: 56 percent / NH3 / methanol / 14 h / 85 °C
View Scheme
Multi-step reaction with 2 steps
1: boron trichloride / dichloromethane / 5.5 h / -78 - -20 °C
2: ammonia / methanol / 14 h / 85 °C / Autoclave
View Scheme
methanolic ammonia

methanolic ammonia

4-chloro-7-[2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine
443642-33-9

4-chloro-7-[2-C-methyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

2-O-acetyl-3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-ribofuranose
168427-36-9

2-O-acetyl-3,5-bis-O-(2,4-dichlorophenylmethyl)-1-O-methyl-α-D-ribofuranose

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: methanol; potassium carbonate / 0.75 h / 20 °C
2.1: Dess-Martin periodane / dichloromethane / 73 h / 0 - 20 °C / Inert atmosphere
3.1: diethyl ether / 7 h / -55 - -15 °C
3.2: 0.5 h / 20 °C / Cooling with ice
4.1: hydrogen bromide; acetic acid / dichloromethane / 4 h / 0 - 20 °C
4.2: 24 h / 20 °C
5.1: boron trichloride / dichloromethane / 5.5 h / -78 - -20 °C
6.1: ammonia / methanol / 14 h / 85 °C / Autoclave
View Scheme
acetyl chloride
75-36-5

acetyl chloride

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-amino-pyrrolo[2,3-d]pyrimidin-7-yl)-3-methyl-tetrahydro-furan-3-yl ester
887747-99-1

acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(4-amino-pyrrolo[2,3-d]pyrimidin-7-yl)-3-methyl-tetrahydro-furan-3-yl ester

Conditions
ConditionsYield
In acetic acid at 20℃;94%
In acetic acid at 20℃;94%
benzoyl chloride
98-88-4

benzoyl chloride

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

C19H20N4O5
1417563-98-4

C19H20N4O5

Conditions
ConditionsYield
Stage #1: 7-deaza-2'-C-methyl-adenosine With pyridine; chloro-trimethyl-silane for 0.25h;
Stage #2: benzoyl chloride at 20℃; for 2h;
Stage #3: With ammonia In water for 0.5h;
54%
7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

4-amino-5-chloro-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

4-amino-5-chloro-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With N-chloro-succinimide In N,N-dimethyl-formamide at 20℃; for 2h;48%
With N-chloro-succinimide In DMF (N,N-dimethyl-formamide) at 20℃; for 1h;
With N-chloro-succinimide In N,N-dimethyl-formamide at 0 - 20℃; for 1h;55 mg
phenyl(isopropoxy-L-alaninyl) phosphorochloridate
261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

7-deaza-2'-C-methyladenosine 5'-O-[phenyl-(isopropoxy-L-alaninyl)]phosphate

7-deaza-2'-C-methyladenosine 5'-O-[phenyl-(isopropoxy-L-alaninyl)]phosphate

Conditions
ConditionsYield
Stage #1: 7-deaza-2'-C-methyl-adenosine With pyridine; 1-methyl-1H-imidazole In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: phenyl(isopropoxy-L-alaninyl) phosphorochloridate In tetrahydrofuran at 20℃; Inert atmosphere;
46%
7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

4-amino-5-bromo-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

4-amino-5-bromo-7-(2-C-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;43%
With N-Bromosuccinimide In DMF (N,N-dimethyl-formamide) at 0 - 10℃; for 0.5h;
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;13 mg
phenyl(benzyloxy-L-alaninyl)phosphorochloridate
183370-70-9

phenyl(benzyloxy-L-alaninyl)phosphorochloridate

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

7-deaza-2'-C-methyladenosine 5'-O-[phenyl-(benzyloxy-L-alaninyl)]phosphate

7-deaza-2'-C-methyladenosine 5'-O-[phenyl-(benzyloxy-L-alaninyl)]phosphate

Conditions
ConditionsYield
Stage #1: 7-deaza-2'-C-methyl-adenosine With pyridine; 1-methyl-1H-imidazole In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: phenyl(benzyloxy-L-alaninyl)phosphorochloridate In tetrahydrofuran at 20℃; Inert atmosphere;
40%
acetic anhydride
108-24-7

acetic anhydride

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

7-deaza-2'-C-methyl-5'-O-trimethylsilyl-2',3'-O-N6-triacetyladenosine
1402064-60-1

7-deaza-2'-C-methyl-5'-O-trimethylsilyl-2',3'-O-N6-triacetyladenosine

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; 7-deaza-2'-C-methyl-adenosine In pyridine at 20℃;
Stage #2: acetic anhydride In pyridine at 20℃; for 3h;
Stage #3: With dmap; triethylamine In pyridine at 45 - 50℃;
acetone
67-64-1

acetone

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

[(3aR,4R,6R,6aR)-6-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2,6a-trimethyltetrahydrofuro[3,4-d][1,3 ]dioxol-4-yl]methanol
862188-59-8

[(3aR,4R,6R,6aR)-6-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2,6a-trimethyltetrahydrofuro[3,4-d][1,3 ]dioxol-4-yl]methanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid; orthoformic acid triethyl ester In DMF (N,N-dimethyl-formamide); water at 20 - 80℃; for 3h;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

acetic anhydride
108-24-7

acetic anhydride

7-deaza-2'-C-methyl-adenosine
443642-29-3

7-deaza-2'-C-methyl-adenosine

7-deaza-2'-C-methyl-5'-O-trimethylsilyl-2',3'-O-N6-triacetyladenosine
1402064-60-1

7-deaza-2'-C-methyl-5'-O-trimethylsilyl-2',3'-O-N6-triacetyladenosine

Conditions
ConditionsYield
Stage #1: chloro-trimethyl-silane; 7-deaza-2'-C-methyl-adenosine In pyridine at 20℃;
Stage #2: acetic anhydride In pyridine at 20℃; for 3h;
Stage #3: With dmap; triethylamine In pyridine at 45 - 50℃;

443642-29-3Relevant articles and documents

NUCLEOSIDE DERIVATIVES AS INHIBITORS OF RNA-DEPENDENT RNA VIRAL POLYERMASE

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, (2017/07/14)

The present invention provides nucleoside compounds and certain derivatives thereof which are inhibitors of RNA-dependent RNA viral polymerase. These compounds are inhibitors of RNA-dependent RNA viral replication and are useful for the treatment of RNA-dependent RNA viral infection. They are particularly useful as inhibitors of hepatitis C virus (HCV) NS5B polymerase, as inhibitors of HCV replication, and/or for the treatment of hepatitis C infection. The invention also describes pharmaceutical compositions containing such nucleoside compounds alone or in combination with other agents active against RNA-dependent RNA viral infection, in particular HCV infection. Also disclosed are methods of inhibiting RNA-dependent RNA polymerase, inhibiting RNA-dependent RNA viral replication, and/or treating RNA-dependent RNA viral infection with the nucleoside compounds of the present invention.

TRICYCLIC-NUCLEOSIDE COMPOUNDS FOR TREATING VIRAL INFECTIONS

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Page/Page column 45, (2009/03/07)

Disclosed are tricyclic nucleoside compounds of formula (I), and methods thereof for treating viral infections mediated at least in part by a Flaviviridae family virus.

Oligonucleotides having modified nucleoside units

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, (2008/06/13)

Disclosed are oligonucleotide that include one or more modified nucleoside units. The oligonucleotides are particularly useful as antisense agents, ribozymes, aptamer, siRNA agents, probes and primers or, when hybridized to an RNA, as a substrate for RNA cleaving enzymes including RNase H and dsRNase.

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