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443642-29-3

Basic Information
CAS No.: 443642-29-3
Name: Lamevudine
Article Data: 11
Molecular Structure:
Molecular Structure of 443642-29-3 (Lamevudine)
Formula: C12H16 N4 O4
Molecular Weight: 280.283
Synonyms: 7-Deaza-2'-C-methyladenosine;MK 0608
Density: 1.75±0.1 g/cm3(Predicted)
Melting Point: 222 °C(Solv: methanol (67-56-1); acetonitrile (75-05-8))
Boiling Point: 620.7±55.0 °C(Predicted)
PSA: 126.65000
LogP: -0.40370
Synthetic route
443642-33-9

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

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%
1053646-61-9

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

443642-29-3

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

Conditions
ConditionsYield
With N-butylamine In methanol; toluene at 64℃;25 g
1027082-25-2

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

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

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
741686-49-7

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

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

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
741686-50-0

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

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

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
943638-20-8

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

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

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
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