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136470-78-5

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136470-78-5 Usage

Description

The drug is extensively metabolized via stepwise phosphorylation to 5′-mono-, di-, and triphosphate. Abacavir is well absorbed (>75%) and penetrates the CNS. The drug can be taken without regard to meals. The drug does not show any clinically significant drug–drug interactions. Abacavir has been reported to produce life-threatening hypersensitivity reactions. The major use of abacavir appears to be in combination with other nucleoside RT inhibitors. A fixed-combination product has recently been approved by the U.S. FDA consisting of 300 mg of ABC, 150 mg of 3TC, and 300 mg of ZDV (Trizivar). The combination has been shown to be superior to other combinations in reducing viral load as well as to show improvement in CD4 cell count.

Originator

Ziagen ,GlaxoSmithKline

Uses

Different sources of media describe the Uses of 136470-78-5 differently. You can refer to the following data:
1. Abacavir is a commonly used nucleoside analogue with potent antiviral activity against HIV-1. - See more at: http://www.selleckchem.com/products/abacavir-sulfate.html#sthash.lApvcTNO.dpuf
2. A nucleoside reverse transcriptase inhibitor (NRTI).

Indications

Abacavir (Ziagen) is a guanosine nucleoside analogue indicated for the therapy of HIV-1 infection in adults and children. It is used as part of a multidrug regimen and is available in a fixed-dose combination with zidovudine and lamivudine (Trizivir). It is also used for postexposure HIV infection prophylaxis.

Manufacturing Process

Treatment of 2,5-diamino-4,6-dihydroxypyrimidine (I) with (chloromethylene)dimethylammonium chloride yielded the dichloropyrimidine with both amino groups derivatized as amidines. Partial hydrolysis with aqueous HCl in hot ethanol gave N-(2-amino-4,6-dichloro-pyrimidin-5-yl)-N,Ndimethylformamidene (II). Subseqent buffered hydrolysis at pH 3.2 yielded the (2-amino-4,6-dichloro-pyrimididin-5-ylamino)acetaldehyde (III). Condensation chloropyrimidine (III) with (1S,4R)-4-amino-2-cyclopentene-1- methanol (IV) in the presence of triethylamine and NaOH gave [2-amino-4- chloro-6-(4-hydroxymethyl-cyclopent-2-enylamino)pyrimidin-5-ylamino]- acetaldehyde (V). The correct enantiomer (IV) of racemic aminocyclopentene was obtained by resolution of diastereomeric salts with D-dibenzoyltartaric acid. Cyclization of (V) to the corresponding purine was accomplished with refluxing triethyl orthoformate or diethoxymethyl acetate to give nucleoside analogue [4-(2-amino-6-chloro-purin-9-yl)-cyclopent-2-enyl]methanol (VI). Displacement of chloride in the purine nucleus with cyclopropyl amine in refluxing butanol afforded abacavir. The structure of obtained compound was confirmed by 1H NMR method and elemental analysis. In practice it is usually used as sulfate salt.

Therapeutic Function

Antiviral

Antimicrobial activity

Abacavir has activity against HIV-1, HIV-2 and human T-cell lymphotrophic virus type-1 (HTLV-1).

Acquired resistance

Resistance is associated with specific changes in codons 184 with 65, 74 or 115 in the HIV reverse transcriptase codon region.

General Description

Abacavir is a nucleoside reverse transcriptase inhibitorNRTI that has been approved for use in combination therapiesfor the treatment of HIV and AIDS. Once in the tissues,it is metabolized by stepwise phosphorylation to themonophosphate, diphosphate, and triphosphate. Abacavir ishighly bioavailable (>75%) and is effective by the oralroute. It penetrates the blood-brain barrier efficiently.Abacavir has been reported to produce life-threatening hypersensitivityreactions in some patients.

Pharmaceutical Applications

A synthetic analog of guanine formulated for oral use.

Pharmacokinetics

Oral absorption: 83% Cmax 300 mg oral, twice daily: 3.0 ± 0.89 mg/L 600 mg once daily: 4.26 mg/L Plasma half-life: 1.5 h Volume of distribution: 0.8 L/kg Plasma protein binding: c. 49% Absorption After oral administration abacavir sulfate undergoes rapid and extensive absorption unaffected by food. Distribution It penetrates well into the cerebrospinal fluid (CSF) and is an NRTI of choice if this characteristic is thought desirable. Good penetration into the male genital tract has been observed. The drug is secreted into human breast milk. Metabolism It is primarily metabolized in the liver, mainly by alcohol dehydrogenase and glucuronidation. Excretion Around 83% of the dose is eliminated in the urine, <2% as unchanged drug; the remainder is excreted in the feces. Dose adjustment is unnecessary in renal impairment. It can be used in moderate hepatic impairment, but is contraindicated if dysfunction is severe.

Clinical Use

Treatment of HIV infection in adults and children (in combination with other antiretroviral drugs)

Side effects

Different sources of media describe the Side effects of 136470-78-5 differently. You can refer to the following data:
1. Abacavir is associated with side effects such as anorexia, nausea, vomiting, malaise, headache, and insomnia. A potentially fatal hypersensitivity reaction develops in approximately 5% of patients, usually early in the course of treatment. Fever and rash are the most common symptoms of this reaction; malaise, respiratory symptoms, and gastrointestinal complaints may also occur. Resistance to abacavir may be associated with resistance to zidovudine, didanosine, and lamivudine.
2. Life-threatening hypersensitivity reactions occur in 5–8% of all individuals, necessitating discontinuation of the drug. Typically patients present within the first 6 weeks of starting treatment with fever, rash or other symptoms that worsen in severity with continued drug exposure. Hypersensitivity is associated with carriage of the major histocompatibility complex class I allele HLA-B57*01 and screening for this allele can significantly reduce the incidence of this effect. Current or recent (within the preceding 6 months) use of abacavir has been associated with a risk of myocardial infarction, but studies have yielded conflicting data.

Drug interactions

Potentially hazardous interactions with other drugs Antivirals: possibly reduces effects of ribavirin; concentration reduced by tipranavir. Orlistat: absorption possibly reduced by orlistat.

Metabolism

Abacavir is primarily metabolised by the liver with approximately 2% of the administered dose being renally excreted, as unchanged compound. The primary pathways of metabolism in man are by alcohol dehydrogenase and by glucuronidation to produce the 5'-carboxylic acid and 5'-glucuronide which account for about 66% of the administered dose. The metabolites are excreted in the urine.

Check Digit Verification of cas no

The CAS Registry Mumber 136470-78-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,6,4,7 and 0 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 136470-78:
(8*1)+(7*3)+(6*6)+(5*4)+(4*7)+(3*0)+(2*7)+(1*8)=135
135 % 10 = 5
So 136470-78-5 is a valid CAS Registry Number.
InChI:InChI=1/C14H18N6O/c15-14-18-12(17-9-2-3-9)11-13(19-14)20(7-16-11)10-4-1-8(5-10)6-21/h1,4,7-10,21H,2-3,5-6H2,(H3,15,17,18,19)/t8-,10+/m0/s1

136470-78-5 Well-known Company Product Price

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  • (Code)Product description
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  • Detail
  • TCI America

  • (A2694)  Abacavir  >98.0%(HPLC)(T)

  • 136470-78-5

  • 1g

  • 810.00CNY

  • Detail
  • TCI America

  • (A2694)  Abacavir  >98.0%(HPLC)(T)

  • 136470-78-5

  • 5g

  • 2,790.00CNY

  • Detail

136470-78-5SDS

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 abacavir

1.2 Other means of identification

Product number -
Other names Abacavir

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:136470-78-5 SDS

136470-78-5Synthetic route

(1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol
136522-33-3

(1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol

Cyclopropylamine
765-30-0

Cyclopropylamine

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
In ethanol at 70℃;98%
In ethanol Heating;72%
Stage #1: (1S,4R)-4-[2-amino-6-chloro-9H-purin-9-yl]-2-cyclopentene-1-methanol; Cyclopropylamine In butan-1-ol at 40 - 70℃; for 5h;
Stage #2: With sodium hydrogencarbonate In butan-1-ol at 20 - 25℃; for 1h; Product distribution / selectivity;
In butan-1-ol at 45 - 90℃; for 2h; Product distribution / selectivity;
With sodium hydrogencarbonate In ethanol; chloroform0.43 g (80%)
Cyclopropylamine
765-30-0

Cyclopropylamine

(1S,cis)-4-(2-amino-6-chloro-9-H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride
172015-79-1

(1S,cis)-4-(2-amino-6-chloro-9-H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
In methanol at 70℃; for 12h; Substitution;90%
Stage #1: (1S,cis)-4-(2-amino-6-chloro-9-H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride With triethylamine In water
Stage #2: Cyclopropylamine In water at 70 - 75℃; Concentration; Solvent; Temperature;
90%
In isopropyl alcohol at 90 - 95℃; for 12h; sealed reactor;
In ethanol at 25 - 78℃; for 6h;
With sodium carbonate In ethanol at 70 - 80℃;25 g
(-)-N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide
136470-88-7

(-)-N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Stage #1: (-)-N-{6-(cyclopropylamino)-9-[(1R,4S)-4-(hydroxymethyl)cyclopent-2-enyl]-9H-purin-2-yl}isobutyramide With isopropyl alcohol; sodium hydroxide for 1h; Reflux;
Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20 - 25℃; pH=7.0 - 7.5; Product distribution / selectivity;
90%
With sodium hydroxide; water; isopropyl alcohol for 1h; Heating / reflux;77%
With sodium hydroxide; water; isopropyl alcohol for 1h; Product distribution / selectivity; Heating / reflux;43%
pyrographite
7440-44-0

pyrographite

Cyclopropylamine
765-30-0

Cyclopropylamine

(1S,cis)-4-(2-amino-6-chloro-9-H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride
172015-79-1

(1S,cis)-4-(2-amino-6-chloro-9-H-purin-9-yl)-2-cyclopentene-1-methanol hydrochloride

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
With sodium hydroxide In acetone90%
6-cyclopropylamine-9-((1R,4S)-4-((triisopropylsilyloxy)methyl)cyclopent-2-enyl)-9H-purin-2-amine
1067882-78-3

6-cyclopropylamine-9-((1R,4S)-4-((triisopropylsilyloxy)methyl)cyclopent-2-enyl)-9H-purin-2-amine

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; water In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;89%
{(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol sulphate

{(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol sulphate

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
With sodium hydroxide In water; ethyl acetate at 25 - 45℃; pH=6 - 6.1;78%
((1S,4R)-4-(6-(cyclopropylamino)-2-((4-methoxybenzyl)amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol
1360538-03-9

((1S,4R)-4-(6-(cyclopropylamino)-2-((4-methoxybenzyl)amino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform at 50℃; for 72h; Inert atmosphere;73%
N6-cyclopropyl-N2-(4-methoxybenzyl)-9-((1R,4S)-4-(((triisopropylsilyl)oxy)methyl)cyclopent-2-en-1-yl)-9H-purine-2,6-diamine

N6-cyclopropyl-N2-(4-methoxybenzyl)-9-((1R,4S)-4-(((triisopropylsilyl)oxy)methyl)cyclopent-2-en-1-yl)-9H-purine-2,6-diamine

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 60℃; for 60h; Schlenk technique;70%
((1S,4R)-4-(2-chloro-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol
1108600-46-9

((1S,4R)-4-(2-chloro-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
With ammonium hydroxide; copper(l) iodide In ethanol at 150℃; for 40h; Schlenk technique; Sealed tube;63%
Stage #1: ((1S,4R)-4-(2-chloro-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol With hydrazine In methanol; water at 50℃;
Stage #2: With acetic acid; sodium nitrite In water at 0℃; for 1h;
Stage #3: With tin(ll) chloride In ethanol for 2h; Product distribution / selectivity; Heating / reflux;
Stage #1: ((1S,4R)-4-(2-chloro-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methanol With hydrazine In methanol at 50℃;
Stage #2: With acetic acid; sodium nitrite In water at 0℃; for 1h;
Stage #3: With ammonia; triphenylphosphine In 1,4-dioxane; water for 5h; Product distribution / selectivity; Heating / reflux;
Multi-step reaction with 2 steps
1: dimethyl sulfoxide / 150 °C
2: trifluoroacetic acid / chloroform / 72 h / 50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: hydrazine hydrate / methanol / 50 °C
2: acetic acid; sodium nitrite / water / 1 h / Cooling with ice
3: stannous chloride dihydrate / ethanol / 2 h / Reflux
View Scheme
Cyclopropylamine
765-30-0

Cyclopropylamine

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene
171887-04-0

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene

A

(1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol
141271-12-7

(1S, 4R)-(4-(2,5-diamino-6-chloro-4-pyrimidinyl)amino)-2-cyclopenten-1-methanol

B

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
In butan-1-ol at 130℃; for 21h; Substitution; hydrolysis;A 16%
B 60%
2-Amino-6-chloropurin
10310-21-1

2-Amino-6-chloropurin

Cyclopropylamine
765-30-0

Cyclopropylamine

cis-3-benzoyloxy-4-(hydroxymethyl)cyclopentene
268737-86-6

cis-3-benzoyloxy-4-(hydroxymethyl)cyclopentene

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Stage #1: 2-Amino-6-chloropurin; cis-3-benzoyloxy-4-(hydroxymethyl)cyclopentene With 1,2,2,6,6-pentamethylpiperidine; tris(dibenzylideneacetone)dipalladium (0); triphenylphosphine In tetrahydrofuran; dimethyl sulfoxide at 45℃; for 16h; Solid phase reaction; addition; elimination;
Stage #2: Cyclopropylamine With N-ethyl-N,N-diisopropylamine In butan-1-ol at 80℃; for 4h; Solid phase reaction; amination; Further stages.;
60%
(+/-)-cis-N-[4-chloro-5-formamido-6-[[4-(hydroxymethyl)-2-cyclopentene-1-yl]amino]-2-pyrimidinyl]acetamide

(+/-)-cis-N-[4-chloro-5-formamido-6-[[4-(hydroxymethyl)-2-cyclopentene-1-yl]amino]-2-pyrimidinyl]acetamide

ethanesulfonic acid
594-45-6

ethanesulfonic acid

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

Cyclopropylamine
765-30-0

Cyclopropylamine

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
In hydrogenchloride; methanol; N,N-dimethyl-formamide19%
((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl acetate
178456-36-5

((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl acetate

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
With sodium hydroxide; water Yield given;
With sodium hydroxide at 20℃;0.027 g
With sodium hydroxide
(1R,5R)-5-hydroxymethyl-2-cyclopenten-1-ol
143395-28-2

(1R,5R)-5-hydroxymethyl-2-cyclopenten-1-ol

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / Et3N; DMAP / CH2Cl2 / 0 °C
2: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
3: aq. NaOH
View Scheme
Multi-step reaction with 4 steps
1: 90 percent / Et3N; DMAP / CH2Cl2 / 0 °C
2: 0.298 g / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
3: ethanol / 5 h / Heating
4: aq. NaOH
View Scheme
Multi-step reaction with 4 steps
1.1: Et3N
2.1: Et3N; 4-DMAP
3.1: aq. HF / acetonitrile
4.1: Pd2(dba)3; PPh3; 1,2,2,6,6-pentamethylpiperidine (pempidine) / tetrahydrofuran; dimethylsulfoxide / 16 h / 45 °C
4.2: 60 percent / EtN(i-Pr)2 / butan-1-ol / 4 h / 80 °C
View Scheme
2-amino-6-(cyclopropylamino)purine
120503-69-7

2-amino-6-(cyclopropylamino)purine

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
2: aq. NaOH
View Scheme
2-Amino-6-chloropurin
10310-21-1

2-Amino-6-chloropurin

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dimethylsulfoxide / 16 h / 55 °C
2: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
3: aq. NaOH
View Scheme
9-[cis-(1'R,4'S)-4'-acetoxymethyl-2'-cyclopenten-1'-yl]-9H-2-amino-6-chloropurine
162992-44-1

9-[cis-(1'R,4'S)-4'-acetoxymethyl-2'-cyclopenten-1'-yl]-9H-2-amino-6-chloropurine

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol / 5 h / Heating
2: aq. NaOH
View Scheme
Multi-step reaction with 2 steps
1: ethanol
2: NaOH, H2O
View Scheme
(1R,2R)-2-acetoxy-1-(acetoxymethyl)-3-cyclopentene
178456-34-3

(1R,2R)-2-acetoxy-1-(acetoxymethyl)-3-cyclopentene

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
2: aq. NaOH
View Scheme
Multi-step reaction with 3 steps
1: 0.298 g / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
2: ethanol / 5 h / Heating
3: aq. NaOH
View Scheme
Multi-step reaction with 2 steps
1: 62 percent / NaH, Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide
2: NaOH, H2O
View Scheme
Multi-step reaction with 3 steps
1: 65 percent / NaH, Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide
2: ethanol
3: NaOH, H2O
View Scheme
[3(1R,2R),4S]-4-benzyl-3-(2-hydroxycyclopent-3-enecarbonyl)oxazolidin-2-one
178327-18-9

[3(1R,2R),4S]-4-benzyl-3-(2-hydroxycyclopent-3-enecarbonyl)oxazolidin-2-one

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78 percent / LiBH4 / tetrahydrofuran; methanol / 1 h / 0 °C
2: 90 percent / Et3N; DMAP / CH2Cl2 / 0 °C
3: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
4: aq. NaOH
View Scheme
Multi-step reaction with 5 steps
1: 78 percent / LiBH4 / tetrahydrofuran; methanol / 1 h / 0 °C
2: 90 percent / Et3N; DMAP / CH2Cl2 / 0 °C
3: 0.298 g / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
4: ethanol / 5 h / Heating
5: aq. NaOH
View Scheme
Multi-step reaction with 4 steps
1: 78 percent / LiBH4 / tetrahydrofuran; methanol
2: 90 percent / Et3N, DMAP / CH2Cl2
3: 62 percent / NaH, Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide
4: NaOH, H2O
View Scheme
Multi-step reaction with 5 steps
1: 78 percent / LiBH4 / tetrahydrofuran; methanol
2: 90 percent / Et3N, DMAP / CH2Cl2
3: 65 percent / NaH, Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide
4: ethanol
5: NaOH, H2O
View Scheme
[3(2S,4R),4S]-3-(2-allyl-3-hydroxypent-4-enoyl)-4-benzyloxazolidin-2-one
178327-17-8

[3(2S,4R),4S]-3-(2-allyl-3-hydroxypent-4-enoyl)-4-benzyloxazolidin-2-one

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 97 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 0.5 h / 25 °C
2: 78 percent / LiBH4 / tetrahydrofuran; methanol / 1 h / 0 °C
3: 90 percent / Et3N; DMAP / CH2Cl2 / 0 °C
4: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
5: aq. NaOH
View Scheme
Multi-step reaction with 6 steps
1: 97 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 0.5 h / 25 °C
2: 78 percent / LiBH4 / tetrahydrofuran; methanol / 1 h / 0 °C
3: 90 percent / Et3N; DMAP / CH2Cl2 / 0 °C
4: 0.298 g / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
5: ethanol / 5 h / Heating
6: aq. NaOH
View Scheme
Multi-step reaction with 5 steps
1: 97 percent / Grubbs catalyst / CH2Cl2
2: 78 percent / LiBH4 / tetrahydrofuran; methanol
3: 90 percent / Et3N, DMAP / CH2Cl2
4: 62 percent / NaH, Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide
5: NaOH, H2O
View Scheme
Multi-step reaction with 6 steps
1: 97 percent / Grubbs catalyst / CH2Cl2
2: 78 percent / LiBH4 / tetrahydrofuran; methanol
3: 90 percent / Et3N, DMAP / CH2Cl2
4: 65 percent / NaH, Pd(PPh3)4 / tetrahydrofuran; dimethylsulfoxide
5: ethanol
6: NaOH, H2O
View Scheme
[4S,2R,3R]-(4-benzyl-2-thioxooxazolidin-3-yl)(2-hydroxycyclopent-3-enyl)methanone
268737-90-2

[4S,2R,3R]-(4-benzyl-2-thioxooxazolidin-3-yl)(2-hydroxycyclopent-3-enyl)methanone

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 85 percent / LiBH4 / tetrahydrofuran; methanol
2: 90 percent / Et3N; DMAP / CH2Cl2 / 0 °C
3: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
4: aq. NaOH
View Scheme
Multi-step reaction with 5 steps
1: 85 percent / LiBH4 / tetrahydrofuran; methanol
2: 90 percent / Et3N; DMAP / CH2Cl2 / 0 °C
3: 0.298 g / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
4: ethanol / 5 h / Heating
5: aq. NaOH
View Scheme
Multi-step reaction with 5 steps
1.1: 78 percent / LiBH4 / methanol
2.1: Et3N
3.1: Et3N; 4-DMAP
4.1: aq. HF / acetonitrile
5.1: Pd2(dba)3; PPh3; 1,2,2,6,6-pentamethylpiperidine (pempidine) / tetrahydrofuran; dimethylsulfoxide / 16 h / 45 °C
5.2: 60 percent / EtN(i-Pr)2 / butan-1-ol / 4 h / 80 °C
View Scheme
(E)-(2R,3R)-2-Allyl-hex-4-ene-1,3-diol
318488-34-5

(E)-(2R,3R)-2-Allyl-hex-4-ene-1,3-diol

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Et3N / CH2Cl2
2: (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 25 °C
3: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
4: aq. NaOH
View Scheme
Multi-step reaction with 5 steps
1: Et3N / CH2Cl2
2: (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 25 °C
3: 0.298 g / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
4: ethanol / 5 h / Heating
5: aq. NaOH
View Scheme
Acetic acid (1R,2R)-2-acetoxymethyl-1-((E)-propenyl)-pent-4-enyl ester

Acetic acid (1R,2R)-2-acetoxymethyl-1-((E)-propenyl)-pent-4-enyl ester

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 25 °C
2: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
3: aq. NaOH
View Scheme
Multi-step reaction with 4 steps
1: (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 25 °C
2: 0.298 g / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
3: ethanol / 5 h / Heating
4: aq. NaOH
View Scheme
(E)-(2S,3R)-2-Allyl-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-hex-4-en-1-one
318488-32-3

(E)-(2S,3R)-2-Allyl-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-hex-4-en-1-one

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 77 percent / NaBH4 / tetrahydrofuran; H2O
2: Et3N / CH2Cl2
3: (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 25 °C
4: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
5: aq. NaOH
View Scheme
Multi-step reaction with 6 steps
1: 77 percent / NaBH4 / tetrahydrofuran; H2O
2: Et3N / CH2Cl2
3: (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 25 °C
4: 0.298 g / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
5: ethanol / 5 h / Heating
6: aq. NaOH
View Scheme
(E)-(2S,3R)-2-Allyl-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-hex-4-en-1-one
318488-35-6

(E)-(2S,3R)-2-Allyl-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-hex-4-en-1-one

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 74 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 1 h / 40 °C
2: 85 percent / LiBH4 / tetrahydrofuran; methanol
3: 90 percent / Et3N; DMAP / CH2Cl2 / 0 °C
4: 62 percent / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
5: aq. NaOH
View Scheme
Multi-step reaction with 6 steps
1: 74 percent / (Cy3P)2Cl2Ru=CHPh / CH2Cl2 / 1 h / 40 °C
2: 85 percent / LiBH4 / tetrahydrofuran; methanol
3: 90 percent / Et3N; DMAP / CH2Cl2 / 0 °C
4: 0.298 g / NaH; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 45 °C
5: ethanol / 5 h / Heating
6: aq. NaOH
View Scheme
(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclopent-2-enol
268737-91-3

(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclopent-2-enol

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: Et3N; 4-DMAP
2.1: aq. HF / acetonitrile
3.1: Pd2(dba)3; PPh3; 1,2,2,6,6-pentamethylpiperidine (pempidine) / tetrahydrofuran; dimethylsulfoxide / 16 h / 45 °C
3.2: 60 percent / EtN(i-Pr)2 / butan-1-ol / 4 h / 80 °C
View Scheme
Benzoic acid (1R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopent-2-enyl ester
268737-92-4

Benzoic acid (1R,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopent-2-enyl ester

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: aq. HF / acetonitrile
2.1: Pd2(dba)3; PPh3; 1,2,2,6,6-pentamethylpiperidine (pempidine) / tetrahydrofuran; dimethylsulfoxide / 16 h / 45 °C
2.2: 60 percent / EtN(i-Pr)2 / butan-1-ol / 4 h / 80 °C
View Scheme
(2S,3R)-2-Allyl-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-pent-4-en-1-one
268737-89-9

(2S,3R)-2-Allyl-1-((R)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-pent-4-en-1-one

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 97 percent / catalytic ring-closing metathesis (RCM)
2.1: 78 percent / LiBH4 / methanol
3.1: Et3N
4.1: Et3N; 4-DMAP
5.1: aq. HF / acetonitrile
6.1: Pd2(dba)3; PPh3; 1,2,2,6,6-pentamethylpiperidine (pempidine) / tetrahydrofuran; dimethylsulfoxide / 16 h / 45 °C
6.2: 60 percent / EtN(i-Pr)2 / butan-1-ol / 4 h / 80 °C
View Scheme
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

abacavir
136470-78-5

abacavir

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.264 g / tetrahydrofuran; H2O / 18 h / 20 - 60 °C
2: 90.5 percent / LiAlH4 / tetrahydrofuran / 19.5 h / 0 °C / Heating
3: 83 percent / Et3N / ethanol / 7 h / Heating
4: 60 percent / butan-1-ol / 21 h / 130 °C
View Scheme
Multi-step reaction with 5 steps
1: 1.264 g / tetrahydrofuran; H2O / 18 h / 20 - 60 °C
2: 90.5 percent / LiAlH4 / tetrahydrofuran / 19.5 h / 0 °C / Heating
3: 83 percent / Et3N / ethanol / 7 h / Heating
4: 92 percent / triethylorthoformate; HCl / H2O / 4 h
5: 90 percent / methanol / 12 h / 70 °C
View Scheme
abacavir
136470-78-5

abacavir

(1R,cis)-3-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-1-cyclopentane-1-methanol

(1R,cis)-3-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-1-cyclopentane-1-methanol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 2585.74 Torr; for 1.5h; Catalytic hydrogenation;98%
ethyl acetate
141-78-6

ethyl acetate

abacavir
136470-78-5

abacavir

((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl acetate
178456-36-5

((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl acetate

Conditions
ConditionsYield
With heterogeneous zinc/imidazole catalyst for 6.5h; Inert atmosphere; Schlenk technique; Reflux; chemoselective reaction;98%
abacavir
136470-78-5

abacavir

{(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol sulphate

{(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]cyclopent-2-en-1-yl}methanol sulphate

Conditions
ConditionsYield
With sulfuric acid In water; isopropyl alcohol at 50 - 55℃; for 2h; Concentration; Temperature; Solvent;95%
maleic acid
110-16-7

maleic acid

abacavir
136470-78-5

abacavir

(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol maleate
1280629-56-2

(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol maleate

Conditions
ConditionsYield
In ethanol at 25 - 30℃; for 0.25h;94.3%
4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

abacavir
136470-78-5

abacavir

[(1S,4R)-4-(6-Cyclopropylamino-2-{[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-purin-9-yl)-cyclopent-2-enyl]-methanol

[(1S,4R)-4-(6-Cyclopropylamino-2-{[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-amino}-purin-9-yl)-cyclopent-2-enyl]-methanol

Conditions
ConditionsYield
With acetic acid microwave irradiation;89%
malonic acid
141-82-2

malonic acid

abacavir
136470-78-5

abacavir

(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol malonate
1280629-49-3

(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol malonate

Conditions
ConditionsYield
In ethanol at 25 - 70℃; for 0.75h; Product distribution / selectivity;88%
5-fluoro-1H-indole-2,3-dione
443-69-6

5-fluoro-1H-indole-2,3-dione

abacavir
136470-78-5

abacavir

3-[(E)-6-Cyclopropylamino-9-((1R,4S)-4-hydroxymethyl-cyclopent-2-enyl)-9H-purin-2-ylimino]-5-fluoro-1,3-dihydro-indol-2-one

3-[(E)-6-Cyclopropylamino-9-((1R,4S)-4-hydroxymethyl-cyclopent-2-enyl)-9H-purin-2-ylimino]-5-fluoro-1,3-dihydro-indol-2-one

Conditions
ConditionsYield
With acetic acid microwave irradiation;87%
2,2,2-trifluoroethyl benzoate
1579-72-2

2,2,2-trifluoroethyl benzoate

abacavir
136470-78-5

abacavir

((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl benzoate

((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl benzoate

Conditions
ConditionsYield
With (μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)] In toluene at 120℃; for 5h; Inert atmosphere; Schlenk technique; chemoselective reaction;87%
11-(acetylthio)undecanoic acid
6974-31-8

11-(acetylthio)undecanoic acid

abacavir
136470-78-5

abacavir

C27H40N6O3S

C27H40N6O3S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; for 5h;85%
1-ethenesulfonyl-piperidine
66089-45-0

1-ethenesulfonyl-piperidine

abacavir
136470-78-5

abacavir

N6-cyclopropyl-9-((1R,4S)-4-((2-(piperidin-1-ylsulfonyl)ethoxy)methyl)cyclopent-2-en-1-yl)-9H-purine-2,6-diamine

N6-cyclopropyl-9-((1R,4S)-4-((2-(piperidin-1-ylsulfonyl)ethoxy)methyl)cyclopent-2-en-1-yl)-9H-purine-2,6-diamine

Conditions
ConditionsYield
Stage #1: abacavir With silver(I) acetate; 1,2-bis-(diphenylphosphino)ethane In N,N-dimethyl-formamide at -20℃; Inert atmosphere;
Stage #2: 1-ethenesulfonyl-piperidine With potassium hexamethylsilazane In tetrahydrofuran; N,N-dimethyl-formamide at -20℃; for 21h; Inert atmosphere; regioselective reaction;
85%
abacavir
136470-78-5

abacavir

(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol dihydrobromide

(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol dihydrobromide

Conditions
ConditionsYield
With hydrogen bromide In ethanol; water at 25 - 30℃; for 0.75h; Product distribution / selectivity;83%
indole-2,3-dione
91-56-5

indole-2,3-dione

abacavir
136470-78-5

abacavir

3-[(E)-6-Cyclopropylamino-9-((1R,4S)-4-hydroxymethyl-cyclopent-2-enyl)-9H-purin-2-ylimino]-1,3-dihydro-indol-2-one

3-[(E)-6-Cyclopropylamino-9-((1R,4S)-4-hydroxymethyl-cyclopent-2-enyl)-9H-purin-2-ylimino]-1,3-dihydro-indol-2-one

Conditions
ConditionsYield
With acetic acid microwave irradiation;82%
abacavir
136470-78-5

abacavir

(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrobromide
1280727-16-3

(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopentene-1-methanol hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In ethanol; water at 25 - 30℃; for 0.75h; Product distribution / selectivity;82%
5-methyl-indole-2,3-dione
608-05-9

5-methyl-indole-2,3-dione

abacavir
136470-78-5

abacavir

3-[(E)-6-Cyclopropylamino-9-((1R,4S)-4-hydroxymethyl-cyclopent-2-enyl)-9H-purin-2-ylimino]-5-methyl-1,3-dihydro-indol-2-one

3-[(E)-6-Cyclopropylamino-9-((1R,4S)-4-hydroxymethyl-cyclopent-2-enyl)-9H-purin-2-ylimino]-5-methyl-1,3-dihydro-indol-2-one

Conditions
ConditionsYield
With acetic acid microwave irradiation;78%
C13H18ClN2O5P

C13H18ClN2O5P

abacavir
136470-78-5

abacavir

(S)-2-{[(1S,4R)-4-(2-Amino-6-cyclopropylamino-purin-9-yl)-cyclopent-2-enylmethoxy]-phenoxy-phosphorylamino}-propionic acid methyl ester
261909-26-6

(S)-2-{[(1S,4R)-4-(2-Amino-6-cyclopropylamino-purin-9-yl)-cyclopent-2-enylmethoxy]-phenoxy-phosphorylamino}-propionic acid methyl ester

Conditions
ConditionsYield
Stage #1: abacavir With tert-butylmagnesium chloride In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: C13H18ClN2O5P In tetrahydrofuran at 20℃; Inert atmosphere;
76%
tert-butoxyacetic acid
13211-32-0

tert-butoxyacetic acid

abacavir
136470-78-5

abacavir

((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl 2-(tert-butoxy)acetate

((1S,4R)-4-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)cyclopent-2-en-1-yl)methyl 2-(tert-butoxy)acetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 25 - 30℃;74%
tetra(n-butyl)ammonium hydroxide
2052-49-5

tetra(n-butyl)ammonium hydroxide

abacavir
136470-78-5

abacavir

C14H17N6O4P(2-)*2C16H36N(1+)

C14H17N6O4P(2-)*2C16H36N(1+)

Conditions
ConditionsYield
Stage #1: abacavir With pyridine; water; trichlorophosphate In acetonitrile at 0℃;
Stage #2: With water; ammonium bicarbonate In acetonitrile at 0℃; pH=8;
Stage #3: tetra(n-butyl)ammonium hydroxide In water; acetonitrile
72%
abacavir
136470-78-5

abacavir

4-Hydroxyacetophenone
99-93-4

4-Hydroxyacetophenone

4-{1-[(E)-6-Cyclopropylamino-9-((1R,4S)-4-hydroxymethyl-cyclopent-2-enyl)-9H-purin-2-ylimino]-ethyl}-phenol

4-{1-[(E)-6-Cyclopropylamino-9-((1R,4S)-4-hydroxymethyl-cyclopent-2-enyl)-9H-purin-2-ylimino]-ethyl}-phenol

Conditions
ConditionsYield
With acetic acid microwave irradiation;71%
tetra(n-butyl)ammonium hydroxide
2052-49-5

tetra(n-butyl)ammonium hydroxide

abacavir
136470-78-5

abacavir

abacavir monophosphate 1.15*nBu4N+ salt

abacavir monophosphate 1.15*nBu4N+ salt

Conditions
ConditionsYield
Stage #1: abacavir With trichlorophosphate at 0℃; for 1h; Inert atmosphere;
Stage #2: With water for 1h; Cooling with ice;
Stage #3: tetra(n-butyl)ammonium hydroxide In water pH=7.0;
71%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

abacavir
136470-78-5

abacavir

[(1S,4R)-4-(6-Cyclopropylamino-2-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-purin-9-yl)-cyclopent-2-enyl]-methanol

[(1S,4R)-4-(6-Cyclopropylamino-2-{[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amino}-purin-9-yl)-cyclopent-2-enyl]-methanol

Conditions
ConditionsYield
With acetic acid microwave irradiation;70%
1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

abacavir
136470-78-5

abacavir

C38H50N12O4

C38H50N12O4

Conditions
ConditionsYield
Stage #1: 1,10-decanedioic acid With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; diisopropylamine In N,N-dimethyl-formamide at -20℃; for 0.333333h;
Stage #2: abacavir In N,N-dimethyl-formamide at -20 - 20℃; for 16h;
70%

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136470-78-5Relevant articles and documents

Abacavir intermediate and method for purifying same

-

, (2018/03/26)

The invention discloses an abacavir intermediate and a method for purifying the same. The method includes heating mixtures with abacavir intermediate crude products, purified water and water-soluble organic solvents until the abacavir intermediate crude products are completely dissolved so as to obtain mixed liquid; carrying out cooling and crystallization treatment on the mixed liquid; carrying out filtering and drying treatment after crystallization treatment is carried out so as to obtain abacavir intermediate pure products. A structural formula of the abacavir intermediate is shown as a formula IV. The abacavir intermediate and the method have the advantage that the method is easy and convenient to implement and is suitable for industrial production.

Enantioselective and Regiodivergent Addition of Purines to Terminal Allenes: Synthesis of Abacavir

Thieme, Niels,Breit, Bernhard

supporting information, p. 1520 - 1524 (2017/02/05)

The rhodium-catalyzed atom-economic asymmetric N-selective intermolecular addition of purine derivatives to terminal allenes is reported. Branched allylic purines were obtained in high yields, regioselectivity and outstanding enantioselectivity utilizing a Rh/Josiphos catalyst. Conversely, linear selective allylation of purines could be realized in good to excellent regio- and E/Z-selectivity with a Pd/dppf catalyst system. Furthermore, the new methodology was applied to a straightforward asymmetric synthesis of carbocyclic nucleoside abacavir.

Enantioselective synthesis of the carbocyclic nucleoside (-)-abacavir

Boyle, Grant A.,Edlin, Christopher D.,Li, Yongfeng,Liotta, Dennis C.,Morgans, Garreth L.,Musonda, Chitalu C.

, p. 1870 - 1876 (2012/05/04)

An enantiopure β-lactam with a suitably disposed electron withdrawing group on nitrogen, participated in a π-allylpalladium mediated reaction with 2,6-dichloropurine tetrabutylammonium salt to afford an advanced cis-1,4-substituted cyclopentenoid with both high regio- and stereoselectivity. This advanced intermediate was successfully manipulated to the total synthesis of (-)-Abacavir.

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