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134678-17-4

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134678-17-4 Usage

Description

Lamivudine is a new generation orally active nucleoside analog launched in the U.S.A. for use in combination with zidovudine (AZT) as a first-line therapy for patients with HIV infection. Lamivudine is rapidly converted to phosphorylated metabolites in the body which act as inhibitors and chain terminators of HIV reverse transcriptase (RT), the enzyme required for the replication of the HIV genome. Lamivudine has similar inhibitory potency to RT as AZT but is 10 times less toxic and is active against AZT-resistant strains of HIV.

Chemical Properties

White Crystalline Powder

Originator

BioChem Pharma (Canada)

Uses

Lamivudine is used along with other medications to treat human immunodeficiency virus (HIV) infection in adults and children 3 months of age and older. Lamivudine (Epivir-HBV) is used to treat hepatitis B infection. Lamivudine is in a class of medications called nucleoside reverse transcriptase inhibitors (NRTIs). It works by decreasing the amount of HIV and hepatitis B in the blood.

Synthesis

Aqueous hydrochloric acid (6N, 30 ml) was slowly added to a solution of 20 gm of the solid (2R-cis)-4-Amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidi- none.S-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate in water (200 ml) at 45-50 deg C. Stirred the reaction for 1 hour at room temperature. The solid S-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate was filtered and the aqueous layer was neutralized with aqueous sodium hydroxide solution (30%, 20 ml). The solvent was recovered under vacuum at 40-45 deg C., the product obtained was dissolved in methanol (200 ml), filtered to remove the inorganic salts, the filtrate was concentrated under vacuum at 40-45 deg C. and the residual solid obtained was dissolved in ethanol (50 ml), heated to 50 deg C., slowly allowed to room temperature, cooled to 10 deg C., filtered and dried at 40-45 deg C. to obtain 5 gm of Lamivudine(Chiral purity: 97.5%).

Definition

ChEBI: Lamivudine is a monothioacetal that consists of cytosine having a (2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl moiety attached at position 1. An inhibitor of HIV-1 reverse transcriptase.

Brand name

Epivir (GlaxoSmithKline).

Acquired resistance

Long-term lamivudine administration frequently elicits viral resistance characterized by a reincrease of viral replication in an adherent patient. The incidence of lamivudine resistance is 14% to 32% after 1 year of treatment, 38% after 2 years, and 53% to 76% after 3 years.

Pharmaceutical Applications

An analog of cytidine available for oral administration.

Pharmacokinetics

The pharmacokinetics of lamivudine are similar in patients with HIV-1 or HBV infection, and healthy volunteers. The drug is rapidly absorbed after oral administration, with maximum serum concentrations usually attained 0.5 to 1.5 hours after the dose.

Clinical Use

Lamivudine is indicated for the treatment of HIV when used in combination with other antiretroviral agents.A lower dose than that used to treat HIV is approved for the treatment of HBV.

Side effects

Lamivudine oral tablet can cause mild or serious side effects. The more common side effects that can occur with lamivudine include:cough,diarrhea,fatigue,headache,malaise (general discomfort),nasal symptoms, such as a runny nose,nausea.

Drug interactions

There are potentially dangerous interactions with other drugs when used in combination.Antimicrobials: trimethoprim inhibits the excretion of lamivudine.Antivirals: avoid concomitant use with foscarnet, emtricitabine, and IV ganciclovirCytotoxic drugs: avoid concomitant use with clarithromycin.Orlistat: absorption may be reduced by orlistat.

Metabolism

Lamivudine is metabolised intracellularly to the active antiviral triphosphate. Hepatic metabolism is low (5-10%) and the majority of lamivudine is excreted unchanged in the urine via glomerular filtration and active secretion (organic cationic transport system).

References

Arts and Wainberg (1996), Mechanism of nucleoside analog antiviral activity and resistance during human immunodeficiency virus reverse transcription; Antimicrob. Agents Chemother., 40 527 Coates et al. (1992), (-)-2’-deoxy-3’-thiacytidine is a potent, highly selective inhibitor of human immunodeficiency virus type 1 and type 2 replication in vitro; Antimicrob. Agents Chemother., 36 733 Kong et al. (2022), Targeted P2X7/NLRP3 signaling pathway against inflammation, apoptosis, and pyroptosis of retinal endothelial cells in diabetic retinopathy; Cell Death Dis., 13 336 Rajukar et al. (2022), Reverse Transcriptase Inhibition Disrupts Repeat Element Life Cycle in Colorectal Cancer; Cancer Discov., 2021 Online ahead of print

Check Digit Verification of cas no

The CAS Registry Mumber 134678-17-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,4,6,7 and 8 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 134678-17:
(8*1)+(7*3)+(6*4)+(5*6)+(4*7)+(3*8)+(2*1)+(1*7)=144
144 % 10 = 4
So 134678-17-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H11N3O3S/c9-5-1-2-11(8(13)10-5)6-4-15-7(3-12)14-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7+/m1/s1

134678-17-4 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (L0217)  Lamivudine  >98.0%(HPLC)(T)

  • 134678-17-4

  • 100mg

  • 590.00CNY

  • Detail
  • TCI America

  • (L0217)  Lamivudine  >98.0%(HPLC)(T)

  • 134678-17-4

  • 1g

  • 2,450.00CNY

  • Detail
  • Sigma-Aldrich

  • (Y0000426)  Lamivudine for system suitability 2  European Pharmacopoeia (EP) Reference Standard

  • 134678-17-4

  • Y0000426

  • 1,880.19CNY

  • Detail

134678-17-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name lamivudine

1.2 Other means of identification

Product number -
Other names Lamivudine

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:134678-17-4 SDS

134678-17-4Synthetic route

C9H11N3O4S*CH4O

C9H11N3O4S*CH4O

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With sodium tetrahydroborate; ethanol at 0 - 20℃; for 4h;97.9%
Carbonic acid (2R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolan-2-ylmethyl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

Carbonic acid (2R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolan-2-ylmethyl ester (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With potassium carbonate In methanol at 0℃; for 10h;95%
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[2-oxo-4-(phenylcarboxamido)-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[2-oxo-4-(phenylcarboxamido)-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[2-oxo-4-(phenylcarboxamido)-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate With methanol at 40℃; Inert atmosphere;
Stage #2: With sodium tetrahydroborate; dipotassium hydrogenphosphate; water; sodium hydroxide In methanol at 20℃; for 1h; diastereoselective reaction;
95%
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carbaxylate
147027-10-9

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carbaxylate

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h; Ambient temperature;94%
With methanol; sodium tetrahydroborate; dipotassium hydrogenphosphate; sodium hydroxide In water at 20℃; for 0.055h; Flow reactor;94%
With sodium tetrahydroborate In ethanol83%
lamivudine salicyclic acid salt
173522-96-8

lamivudine salicyclic acid salt

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With triethylamine In ethanol at 50℃; for 1h;92.63%
With triethylamine In water; ethyl acetate at 25 - 50℃; for 5h; Product distribution / selectivity;
With triethylamine In water; ethyl acetate at 45 - 50℃; for 4.5h;
4-amino-1-[(2R,5S)-(2-hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one (S)-BINOL co-crystal

4-amino-1-[(2R,5S)-(2-hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one (S)-BINOL co-crystal

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
Stage #1: 4-amino-1-[(2R,5S)-(2-hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one (S)-BINOL co-crystal With hydrogenchloride In water; ethyl acetate at 20℃; for 1h; pH=3 - 4;
Stage #2: With sodium hydroxide In water pH=~ 7; Product distribution / selectivity;
90%
With hydrogenchloride In water; ethyl acetate pH=2 - 3; Large scale reaction; optical yield given as %ee;70.02%
With hydrogenchloride In water; ethyl acetate pH=2 - 2.5;
Stage #1: 4-amino-1-[(2R,5S)-(2-hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one (S)-BINOL co-crystal With hydrogenchloride In water; ethyl acetate at 20℃; for 0.0833333h; pH=3 - 4;
Stage #2: With sodium hydroxide In water pH=6.8 - 7.2; Reagent/catalyst;
7 g
In water; ethyl acetate at 2 - 45℃; Industrial scale;33.3 kg
C7H5NO4*C8H11N3O3S

C7H5NO4*C8H11N3O3S

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With triethylamine In ethanol at 70 - 75℃; Inert atmosphere; Industry scale;90%
((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate

((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With potassium carbonate In methanol at 20℃; for 14h; Inert atmosphere;89%
(-)-cis-4-amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one salicylate

(-)-cis-4-amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)-(1H)-pyrimidin-2-one salicylate

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With triethylamine In Isopropyl acetate; water at 23 - 27℃; for 10h; Product distribution / selectivity;88%
(2R,5S)-5-(4
1012053-56-3

(2R,5S)-5-(4"-amino-2"-oxo-pyrimidin-1"-yl)-1,3-oxathiolane-2-methyl-(2'S-isopropyl-5'R-methyl-1'R-cyclohexyl)-carbonic acid diester

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With potassium carbonate In methanol at 0 - 25℃; for 3h;87.17%
With potassium carbonate In methanol at 0 - 25℃; for 2h;86%
(2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>cytosine
145985-97-3

(2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>cytosine

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.5h; Ambient temperature;75%
With tetrabutyl ammonium fluoride In tetrahydrofuran Ambient temperature;75%
Conditions
ConditionsYield
Stage #1: (+/-)-cis-N-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine With (S)-N-acetyl-2-phenylglycine In methanol; acetone at -30 - 0℃; for 48h;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.5h; Product distribution / selectivity;
32%
Stage #1: (+/-)-cis-N-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine With (S)-N-acetyl-2-phenylglycine In methanol; acetone at -30 - 0℃; for 48h; Resolution of racemate;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.5h; Purification / work up;
32%
Multi-step reaction with 3 steps
1: 95 percent / dimethylformamide / 20 °C
2: 50.6 percent / pyridine / acetonitrile / 48 h / 0 °C
3: 95 percent / K2CO3 / methanol / 10 h / 0 °C
View Scheme
Benzoic acid (2R,5S)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolan-2-ylmethyl ester
143957-12-4

Benzoic acid (2R,5S)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolan-2-ylmethyl ester

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With Amberlite IRA400(OH) In ethanol Heating;
Benzoic acid (R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolan-2-ylmethyl ester

Benzoic acid (R)-5-(4-amino-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolan-2-ylmethyl ester

B

lamivudine
134678-17-4

lamivudine

C

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine
139757-68-9

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine

Conditions
ConditionsYield
With Amberlit IRA400 In methanol Heating; Yield given. Yields of byproduct given;
With Amberlit IRA400 In methanol Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate

((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate

B

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With ammonia In methanol Yield given. Title compound not separated from byproducts;
cis-2-(hydroxymethyl)-5-(N4-acetylcytosin-1'-yl)-1,3-oxathiolane

cis-2-(hydroxymethyl)-5-(N4-acetylcytosin-1'-yl)-1,3-oxathiolane

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50.6 percent / pyridine / acetonitrile / 48 h / 0 °C
2: 95 percent / K2CO3 / methanol / 10 h / 0 °C
View Scheme
(2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-acetylcytosine
139757-74-7

(2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-acetylcytosine

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / methanolic NH3 / 3 h / Ambient temperature
2: 75 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 73 percent / NH3 / methanol / Ambient temperature
2: 75 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / Ambient temperature
View Scheme
Conditions
ConditionsYield
Stage #1: (+/-)-cis-N-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine With (S)-N-acetyl-2-phenylglycine In ethanol at -30 - -20℃; for 48h;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.5h; Product distribution / selectivity;
A n/a
B n/a
Stage #1: (+/-)-cis-N-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine With O,O'-dibenzoyl-L-tartaric acid In methanol; acetone at -30 - 20℃; for 48h;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.5h; Product distribution / selectivity;
A n/a
B n/a
Stage #1: (+/-)-cis-N-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine With (S)-N-acetyl-2-phenylglycine In methanol; acetone at -50 - 25℃; for 48h;
Stage #2: With sodium hydroxide In dichloromethane; water for 0.5h; Product distribution / selectivity;
A n/a
B n/a
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carbaxylate
147027-10-9

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carbaxylate

salicylic acid
69-72-7

salicylic acid

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate With sodium tetrahydroborate; dipotassium hydrogenphosphate In ethanol; water at 18 - 22℃; for 8 - 9h;
Stage #2: salicylic acid In water at 10 - 82℃;
(2R)-5-(4'-acetamido-2'-oxo-pyrimidin-1'-yl)-1,3-oxathiolane-2-methyl-(6'-methoxy)-2'(S)-naphthalene isopropionate

(2R)-5-(4'-acetamido-2'-oxo-pyrimidin-1'-yl)-1,3-oxathiolane-2-methyl-(6'-methoxy)-2'(S)-naphthalene isopropionate

A

lamivudine
134678-17-4

lamivudine

B

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine
139757-68-9

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine

Conditions
ConditionsYield
With methanol; potassium carbonate at 20℃;
(2R)-5-(4'-acetamido-2'-oxo-pyrimidin-1'-yl)-1,3-oxathiolane-2-methyl-(2'(R)-hydroxy)phenyl acetate

(2R)-5-(4'-acetamido-2'-oxo-pyrimidin-1'-yl)-1,3-oxathiolane-2-methyl-(2'(R)-hydroxy)phenyl acetate

A

lamivudine
134678-17-4

lamivudine

B

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine
139757-68-9

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine

Conditions
ConditionsYield
With methanol; potassium carbonate at 20℃;
((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate

((2R,5S)-5-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-1,3-oxathiolan-2-yl)methyl benzoate

A

lamivudine
134678-17-4

lamivudine

B

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine
139757-68-9

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine

Conditions
ConditionsYield
With methanol; potassium carbonate at 20℃;
(2R,5S)-5-(4'-acetamido-2'-oxo-pyrimidin-1'-yl)-1,3-oxathiolane-2-methyl-(4'-chloro)-benzoate
1091585-31-7

(2R,5S)-5-(4'-acetamido-2'-oxo-pyrimidin-1'-yl)-1,3-oxathiolane-2-methyl-(4'-chloro)-benzoate

A

lamivudine
134678-17-4

lamivudine

B

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine
139757-68-9

(+)-(2R,5R)-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine

Conditions
ConditionsYield
With methanol; potassium carbonate at 20℃;
(2R-cis)-4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone S-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate

(2R-cis)-4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone S-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
Stage #1: (2R-cis)-4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone S-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate With hydrogenchloride In ethanol; water at 20 - 50℃;
Stage #2: With sodium hydroxide In ethanol; water at 5 - 50℃; pH=7.5; Product distribution / selectivity;
n/a
cis-(+/-)-4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone

cis-(+/-)-4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone

(S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate
35193-63-6, 35193-64-7, 39648-67-4, 50574-52-2

(S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
Stage #1: cis-(+/-)-4-amino-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2(1H)-pyrimidinone; (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate With sodium hydroxide In water at 20 - 45℃;
Stage #2: With hydrogenchloride In ethanol; water at 20℃;
Stage #3: With sodium hydroxide In ethanol; water at 5 - 50℃; pH=7.5; Product distribution / selectivity;
n/a
4-amino-1-[(2R,5S)-2-(hydroxymethyl-1,3-oxathiolane-5-yl)-(1H)]-pyrimidin-2-one dicinnamate

4-amino-1-[(2R,5S)-2-(hydroxymethyl-1,3-oxathiolane-5-yl)-(1H)]-pyrimidin-2-one dicinnamate

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With triethylamine In water; ethyl acetate at 22 - 30℃; for 4.5h;
With triethylamine In ethanol; water at 18 - 80℃;
With triethylamine In water; ethyl acetate at 22 - 30℃; for 4.5h; Product distribution / selectivity;
4-amino-1-[(2R,5S)-2-(hydroxymethyl-1,3-oxathiolane-5-yl)-(1H)]-pyrimidin-2-one succinate

4-amino-1-[(2R,5S)-2-(hydroxymethyl-1,3-oxathiolane-5-yl)-(1H)]-pyrimidin-2-one succinate

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With triethylamine In methanol; water at 22 - 30℃; for 4.5h; Product distribution / selectivity;
With triethylamine In ethanol; ethyl acetate at 47 - 80℃; Product distribution / selectivity;
Lamivudine sulfoxide

Lamivudine sulfoxide

lamivudine
134678-17-4

lamivudine

Conditions
ConditionsYield
With pyridine; tetraphosphorus decasulfide at 22 - 42℃; for 10h; Inert atmosphere;
With pyridine; tetraphosphorus decasulfide at 22 - 42℃; for 10h; Inert atmosphere;
benzoic acid anhydride
93-97-0

benzoic acid anhydride

lamivudine
134678-17-4

lamivudine

N4-benzoyl-1-(2',3'-dideoxy-3'-thia-β-L-ribofuranosyl)-cytosine

N4-benzoyl-1-(2',3'-dideoxy-3'-thia-β-L-ribofuranosyl)-cytosine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 24h;98%
In ethanol at 70℃; for 2.5h; Sealed tube;80%
lamivudine
134678-17-4

lamivudine

triethylammonium α-L-2',3'-dideoxy-3'-thiacytadin-5'-yl phosphonate

triethylammonium α-L-2',3'-dideoxy-3'-thiacytadin-5'-yl phosphonate

Conditions
ConditionsYield
Stage #1: lamivudine With diphenyl hydrogen phosphite In pyridine at 20℃; for 0.5h;
Stage #2: With triethylamine In water
95%
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

lamivudine
134678-17-4

lamivudine

C11H16N4O3S
672313-92-7

C11H16N4O3S

Conditions
ConditionsYield
With pyridine at 20℃; for 24h;95%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

lamivudine
134678-17-4

lamivudine

(-)-5'-O-(t-butyldimethylsilyl)-2',3'-dideoxy-3'-thiacytidine
956896-97-2

(-)-5'-O-(t-butyldimethylsilyl)-2',3'-dideoxy-3'-thiacytidine

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h;95%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;
lamivudine
134678-17-4

lamivudine

triethylamine
121-44-8

triethylamine

triethylammonium α-L-2',3'-dideoxy-3'-thiacytadin-5'-yl phosphonate

triethylammonium α-L-2',3'-dideoxy-3'-thiacytadin-5'-yl phosphonate

Conditions
ConditionsYield
Stage #1: lamivudine With diphenyl hydrogen phosphite In pyridine for 0.5h;
Stage #2: triethylamine With water In pyridine
93%
lamivudine
134678-17-4

lamivudine

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>cytosine
145985-97-3

(2R,5S)-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>cytosine

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 3h; Substitution;90%
lamivudine
134678-17-4

lamivudine

C8H10(125)IN3O3S

C8H10(125)IN3O3S

Conditions
ConditionsYield
With sodium (¹²⁵I)iodide; 1,3,4,6-tetrachloro-3α,6α-diphenyl glycoluril In aq. buffer at 60℃; for 0.166667h; pH=7;89%
2-((2-(((4-nitrophenoxy)carbonyl)oxy)ethyl)disulfanyl)ethyl methacrylate

2-((2-(((4-nitrophenoxy)carbonyl)oxy)ethyl)disulfanyl)ethyl methacrylate

lamivudine
134678-17-4

lamivudine

2-((2-(((lamivudine)carbonyl)oxy)ethyl)disulfanyl)ethyl methacrylate

2-((2-(((lamivudine)carbonyl)oxy)ethyl)disulfanyl)ethyl methacrylate

Conditions
ConditionsYield
With dmap; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;88%
cis-[RuCl2(triphenylphosphine)2(2,2′-bipyridine)]
159593-90-5, 192506-86-8

cis-[RuCl2(triphenylphosphine)2(2,2′-bipyridine)]

sodium perchlorate

sodium perchlorate

lamivudine
134678-17-4

lamivudine

trans-bis(triphenylphosphine)(lamivudinate)(2,2′-bipyridine)ruthenium(II) perchlorate

trans-bis(triphenylphosphine)(lamivudinate)(2,2′-bipyridine)ruthenium(II) perchlorate

Conditions
ConditionsYield
With triethylamine In methanol; dichloromethane for 24h; Reflux; Inert atmosphere;85%
acetic anhydride
108-24-7

acetic anhydride

lamivudine
134678-17-4

lamivudine

4-acetylamino-1-[(2'R,5'S)-2'-(hydroxymethyl)-1,3-oxathiolan-5'-yl]-1,2-dihydropyrimidin-2-one
158704-08-6

4-acetylamino-1-[(2'R,5'S)-2'-(hydroxymethyl)-1,3-oxathiolan-5'-yl]-1,2-dihydropyrimidin-2-one

Conditions
ConditionsYield
Stage #1: lamivudine In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: acetic anhydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
82%
lamivudine
134678-17-4

lamivudine

4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate

4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate

C15H14N4O3S

C15H14N4O3S

Conditions
ConditionsYield
Stage #1: lamivudine With potassium hexamethylsilazane In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: 4-cyano-N,N,N-trimethylanilinium trifluoromethansulfonate In tetrahydrofuran; N,N-dimethyl-formamide at 25℃; for 3h; Inert atmosphere; Schlenk technique;
82%
C8H10O8Pol

C8H10O8Pol

lamivudine
134678-17-4

lamivudine

C24H28N6O12PolS2

C24H28N6O12PolS2

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 60℃; for 7h; solid phase reaction;80%
dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate

dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate

lamivudine
134678-17-4

lamivudine

4-amino-1-((2R,4S)-2-((4-nitrophenoxy)methyl)-1,3-oxathiolan-4-yl)pyrimidin-2(1H)-one

4-amino-1-((2R,4S)-2-((4-nitrophenoxy)methyl)-1,3-oxathiolan-4-yl)pyrimidin-2(1H)-one

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Schlenk technique;75%
ethoxycarbonylphosphonic acid
55920-71-3

ethoxycarbonylphosphonic acid

lamivudine
134678-17-4

lamivudine

3TC 5′-ethoxycarbonyl phosphonate

3TC 5′-ethoxycarbonyl phosphonate

Conditions
ConditionsYield
With pyridine; dicyclohexyl-carbodiimide73%
11-(acetylthio)undecanoic acid
6974-31-8

11-(acetylthio)undecanoic acid

lamivudine
134678-17-4

lamivudine

C21H33N3O5S2

C21H33N3O5S2

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; for 3h;70%
lamivudine
134678-17-4

lamivudine

(2-(2-methoxyethoxy)ethyl) (4-nitrophenyl) carbonate
105108-59-6

(2-(2-methoxyethoxy)ethyl) (4-nitrophenyl) carbonate

C14H21N3O7S
1240259-44-2

C14H21N3O7S

Conditions
ConditionsYield
With 1-hydroxy-pyrrolidine-2,5-dione In N,N-dimethyl-formamide at 20℃; for 72h;63%
Octanoic acid
124-07-2

Octanoic acid

lamivudine
134678-17-4

lamivudine

N4-octanoyl-(−)-L-2',3'-dideoxy-3'-thiacytidine

N4-octanoyl-(−)-L-2',3'-dideoxy-3'-thiacytidine

Conditions
ConditionsYield
Stage #1: Octanoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In dichloromethane; N,N-dimethyl-formamide at 10℃; for 1h;
Stage #2: lamivudine In dichloromethane; N,N-dimethyl-formamide for 20h;
56%
lamivudine
134678-17-4

lamivudine

12-azidododecanoyl chloride
200720-60-1

12-azidododecanoyl chloride

(-)-N(4)-5'-di(12-azidododecanoyl)-2',3'-dideoxy-3'-thiacytidine
1373400-17-9

(-)-N(4)-5'-di(12-azidododecanoyl)-2',3'-dideoxy-3'-thiacytidine

Conditions
ConditionsYield
With dmap In benzene at 100℃; for 4h;55%
lamivudine
134678-17-4

lamivudine

methyl iodide
74-88-4

methyl iodide

4-(dimethylamino)-1-[(2R,5S)-2-(methoxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

4-(dimethylamino)-1-[(2R,5S)-2-(methoxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one

Conditions
ConditionsYield
Stage #1: lamivudine With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; Inert atmosphere;
55%

134678-17-4Related news

Preparation of the enantiomerically enriched precursor of Lamivudine (cas 134678-17-4) (3TC™) via asymmetric catalysis mediated by Klebsiella oxytoca07/31/2019

We report the asymmetric catalysis mediated by a newly isolated strain from soil, Klebsiella oxytoca, for the preparation of the chiral intermediate of antiviral agent lamivudine which is proven to be one of most potent medicines for the treatment of human chronic hepatitis B and HIV infection. ...detailed

Lamivudine (cas 134678-17-4) use in pregnant HBsAg-females effectively reduces maternal viremia07/30/2019

Background and study aimsMother-infant hepatitis B virus (HBV) transmission is the current leading cause of chronic infection. We aimed to assess the efficacy of lamivudine use in hepatitis B surface antigen (HBsAg)-positive pregnant women to decrease viral load and thus aid in the prevention of...detailed

134678-17-4Relevant articles and documents

The chemical resolution of racemic CIS-2-hydroxymethyl-5-(Cytosine-1′-YL)-1,3-oxathiolane (BCH-189) - One direct method to obtain lamivudine as anti-HIV and anti-HBV agent

Li, Ji-zhen,Gao, Lian-xun,Ding, Meng-xian

, p. 2355 - 2359 (2002)

Racemic cis-BCH-189 can be resolved to (-)-enantiomer (lamivudine) and (+)-enantiomer by esterification of cis-2-hydroxymethyl-5-(N′4-acetylcyto sine-1′-yl)-1,3-oxathiolane and (+)-menthyl chloroformate in CH3CN with pyridine as base. The two diastereomers of ester were seperated by recrystallization in methanol at 0°C. Lamivudine was obtained by deprotection of (-)-diastereomer with high yield.

An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly

Abdiaj, Irini,Ahmad, Saeed,Burns, Justina M.,Gopalsamuthiram, Vijayagopal,Gupton, B. Frank,Krack, Rudy,McQuade, D. Tyler,Nelson, Ryan C.,Snead, David R.,Stringham, Rodger W.

, p. 1194 - 1198 (2020)

An economical synthesis of lamivudine was developed by employing a new method to establish the stereochemistry about the heterocyclic oxathiolane ring. Toward this end, an inexpensive and readily accessible lactic acid derivative served the dual purpose of activating the carbohydrate's anomeric center for N-glycosylation and transferring stereochemical information to the substrate simultaneously. Both enantiomers of the lactic acid derivative are available, and either β-enantiomer in this challenging class of 2′-deoxynucleoside active pharmaceutical ingredients can be formed.

Synthesis of an Oxathiolane Drug Substance Intermediate Guided by Constraint-Driven Innovation

Burns, Justina M.,Gupton, B. Frank,Kashinath, K.,McQuade, D. Tyler,Snead, David R.,Stringham, Rodger W.

, p. 2266 - 2270 (2020)

A new route was developed for construction of the oxathiolane intermediate used in the synthesis of lamivudine (3TC) and emtricitabine (FTC). We developed the presented route by constraining ourselves to low-cost, widely available starting materials - we refer to this as supply-centered synthesis. Sulfenyl chloride chemistry was used to construct the framework for the oxathiolane from acyclic precursors. This bond construction choice enabled the use of chloroacetic acid, vinyl acetate, sodium thiosulfate, and water to produce the oxathiolane.

Nucleoside analogs of lamivudine preparation method (by machine translation)

-

Paragraph 0039; 0040; 0044; 0045, (2019/07/11)

The invention relates to a method for the preparation of nucleoside analogs lamivudine. Specific, comprises the following steps: methanol in the solvent, a compound of formula III with a reducing agent, after treatment then outputs II compound, further purification, free, formula I compounds. This method is simple in operation, the resulting high product yield, purity as high as 99.5%. The method of post-processing process is simple, solvent is recycled for future use, in accordance with the needs of industrial production. (by machine translation)

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