Welcome to LookChem.com Sign In|Join Free

CAS

  • or

142217-69-4

Post Buying Request

142217-69-4 Suppliers

Recommended suppliersmore

  • Product
  • FOB Price
  • Min.Order
  • Supply Ability
  • Supplier
  • Contact Supplier

142217-69-4 Usage

Description

Entecavir is a cyclopentyl guanosine analog launched for the once-daily oral treatment of chronic hepatitis B virus (HBV) infection, and it is the third nucleoside or nucleotide analog to be marketed for this indication. Lamivudine, a deoxythiacytosine analog, and adefovir dipivoxil, a nucleotide analog, have been marketed since 1998 and 2002, respectively. Entecavir and adefovir are specifically indicated for HBV, whereas lamivudine is indicated for both HBV and HIV infections.

Chemical Properties

White to Off-White/Yellow Crystalline Powder

Originator

BMS (US)

Uses

Entecavir is a new generation of guanine nucleoside analogues oral medicine for treatment of hepatitis B virus infection in, mainly for the treatment of adult patients with viral replication activity and serum transaminase continued to increase, or liver tissue for pathological activity of chronic hepatitis B, is currently down virus the fastest and the most powerful, the mutation rate lowest nucleoside analogues.

Definition

ChEBI: Guanine substituted at the 9 position by a 4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl group. A synthetic analogue of 2'-deoxyguanosine, it is a nucleoside reverse transcriptase inhibitor with selective antiviral activity against hepatitis B virus Entecavir is phosphorylated intracellularly to the active triphosphate form, which competes with deoxyguanosine triphosphate, the natural substrate of hepatitis B virus reverse transcriptase, inhibiting every stage of the enzyme's activity, although it ha no activity against HIV. It is used for the treatment of chronic hepatitis B.

Mechanism of action

Entecavir is a nucleoside analog, or more specifically, a deoxyguanosine analogue that belongs to a class of carbocyclic nucleosides and inhibits reverse transcription, DNA replication and transcription in the viral replication process.

Pharmacokinetics

Entecavir had a mean terminal half-life ranging from 128 to 149 hours and an effective half-life of approximately 24 hours. Elimination was predominantly through renal excretion, with mean urinary recovery ranging from 62% to 73%.

Clinical Use

Treatment of chronic hepatitis B virus infection in patients >16 years of age.Entecavir comes as a tablet and solution (liquid) to take by mouth. It is usually taken once a day on an empty stomach, at least 2 hours after a meal and at least 2 hours before the next meal. Take entecavir at around the same time every day.

Side effects

The most common side effects of entecavir: the increase of ALT, fatigue, dizziness, nausea, abdominal pain, abdominal discomfort, abdominal discomfort, liver, muscle, insomnia, rubella and indigestion, also be found in neutrophils decreased slightly. These adverse reactions were mild to moderate. It also found that, as the same type of antiviral drugs, entecavir and the first generation of antiviral drugs have similar side effects, such as acid poisoning, hepatomegaly, liver fatty degeneration in the withdrawal will appear rebound phenomenon.

Synthesis

Entecavir is synthesized from 4-trimethylsilyl-3-butyn-2-one and acrolein. The key features of its preparation are: (1) a stereoselective boron–aldol reaction to afford the acyclic carbon skeleton of the methylenecylopentane moiety; (2) its cyclization by a Cp2TiCl-catalyzed intramolecular radical addition of an epoxide to an alkyne; and (3) the coupling with a purine derivative by a Mitsunobu reaction.

Check Digit Verification of cas no

The CAS Registry Mumber 142217-69-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,4,2,2,1 and 7 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 142217-69:
(8*1)+(7*4)+(6*2)+(5*2)+(4*1)+(3*7)+(2*6)+(1*9)=104
104 % 10 = 4
So 142217-69-4 is a valid CAS Registry Number.
InChI:InChI=1/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8+/m0/s1

142217-69-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name Entecavir

1.2 Other means of identification

Product number -
Other names 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one

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:142217-69-4 SDS

142217-69-4Synthetic route

((1 R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl acetate
1383812-22-3

((1 R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl acetate

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Stage #1: ((1 R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl acetate With sodium hydroxide at 80℃; for 2h;
Stage #2: With hydrogenchloride In water at 0℃; pH=7;
60%
(1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-yn-1-ol
1383811-98-0

(1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-yn-1-ol

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: chloro-trimethyl-silane; 2,4,6-trimethyl-pyridine; zinc / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
2.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
3.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
4.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
5.1: sodium hydroxide / 2 h / 80 °C
5.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 6 steps
1.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
2.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
3.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
4.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
5.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
6.1: sodium hydroxide / 2 h / 80 °C
6.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 7 steps
1.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
2.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
3.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
4.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
5.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
5.2: 4.17 h / -10 °C / Inert atmosphere
6.1: formic acid / 9 h / 50 °C / Inert atmosphere
7.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
7.2: pH 7 / Inert atmosphere
View Scheme
(3S,5R)-7-(trimethylsilyl)hept-1-en-6-yne-3,5-diol
1383811-86-6

(3S,5R)-7-(trimethylsilyl)hept-1-en-6-yne-3,5-diol

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 1H-imidazole / tetrahydrofuran / 0 - 15 °C / Inert atmosphere
2.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
4.1: chloro-trimethyl-silane; 2,4,6-trimethyl-pyridine; zinc / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
5.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
6.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
8.1: sodium hydroxide / 2 h / 80 °C
8.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 8 steps
1.1: 1H-imidazole / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere
2.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
4.1: chloro-trimethyl-silane; 2,4,6-trimethyl-pyridine; zinc / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
5.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
6.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
8.1: sodium hydroxide / 2 h / 80 °C
8.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 9 steps
1.1: 1H-imidazole / tetrahydrofuran / 0 - 15 °C / Inert atmosphere
2.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
6.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
7.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
9.1: sodium hydroxide / 2 h / 80 °C
9.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 9 steps
1.1: 1H-imidazole / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere
2.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
6.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
7.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
9.1: sodium hydroxide / 2 h / 80 °C
9.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 10 steps
1.1: 1H-imidazole / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere
2.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
4.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
6.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
7.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
8.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
8.2: 4.17 h / -10 °C / Inert atmosphere
9.1: formic acid / 9 h / 50 °C / Inert atmosphere
10.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
10.2: pH 7 / Inert atmosphere
View Scheme
(3S,5R)-5-(tert-butyldimethylsilyloxy)-7-(trimethylsilyl)hept-1-en-6-yn-3-ol
1383811-90-2

(3S,5R)-5-(tert-butyldimethylsilyloxy)-7-(trimethylsilyl)hept-1-en-6-yn-3-ol

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
3.1: chloro-trimethyl-silane; 2,4,6-trimethyl-pyridine; zinc / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
4.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
6.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
7.1: sodium hydroxide / 2 h / 80 °C
7.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 8 steps
1.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
3.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
4.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
5.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
6.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
8.1: sodium hydroxide / 2 h / 80 °C
8.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 9 steps
1.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
3.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
4.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
5.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
7.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
7.2: 4.17 h / -10 °C / Inert atmosphere
8.1: formic acid / 9 h / 50 °C / Inert atmosphere
9.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
9.2: pH 7 / Inert atmosphere
View Scheme
(3S,5R)-5-(tert-butyldimethylsilyloxy)hept-1-en-6-yn-3-ol
1383811-94-6

(3S,5R)-5-(tert-butyldimethylsilyloxy)hept-1-en-6-yn-3-ol

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
2.1: chloro-trimethyl-silane; 2,4,6-trimethyl-pyridine; zinc / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
3.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
4.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
5.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
6.1: sodium hydroxide / 2 h / 80 °C
6.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 7 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
2.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
3.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
4.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
5.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
6.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
7.1: sodium hydroxide / 2 h / 80 °C
7.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 8 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
2.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
3.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
4.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
6.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
6.2: 4.17 h / -10 °C / Inert atmosphere
7.1: formic acid / 9 h / 50 °C / Inert atmosphere
8.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
8.2: pH 7 / Inert atmosphere
View Scheme
(1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-ynyl acetate
1383812-02-9

(1S,3R)-3-(tert-butyldimethylsilyloxy)-1-(oxiran-2-yl)pent-4-ynyl acetate

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: manganese; 2,4,6-collidine hydrochloride / bis(cyclopentadienyl)titanium dichloride / tetrahydrofuran / 4 h / 20 °C
2.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
3.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
4.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
5.1: sodium hydroxide / 2 h / 80 °C
5.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 6 steps
1.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
2.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
3.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
4.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
4.2: 4.17 h / -10 °C / Inert atmosphere
5.1: formic acid / 9 h / 50 °C / Inert atmosphere
6.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
6.2: pH 7 / Inert atmosphere
View Scheme
(1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-3-methylenecyclopentyl acetate
1383812-06-3

(1S,2R,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-3-methylenecyclopentyl acetate

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
2.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
3.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
4.1: sodium hydroxide / 2 h / 80 °C
4.2: 0 °C / pH 7
View Scheme
Multi-step reaction with 5 steps
1.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
3.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
3.2: 4.17 h / -10 °C / Inert atmosphere
4.1: formic acid / 9 h / 50 °C / Inert atmosphere
5.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
5.2: pH 7 / Inert atmosphere
View Scheme
(1S,2R,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)-3-methylenecyclopentanol
701278-65-1

(1S,2R,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)-3-methylenecyclopentanol

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: dmap; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
2.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
3.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
4.1: sodium hydroxide / 2 h / 80 °C
4.2: 0 °C / pH 7
View Scheme
((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl acetate
1383812-10-9

((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl acetate

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: pyridine; hydrogen fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
3.1: sodium hydroxide / 2 h / 80 °C
3.2: 0 °C / pH 7
View Scheme
((1R,3R,5S)-5-acetoxy-3-hydroxy-2-methylenecyclo-pentyl) methyl acetate

((1R,3R,5S)-5-acetoxy-3-hydroxy-2-methylenecyclo-pentyl) methyl acetate

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triphenylphosphine; di-isopropyl azodicarboxylate / N,N-dimethyl-formamide; tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
2.1: sodium hydroxide / 2 h / 80 °C
2.2: 0 °C / pH 7
View Scheme
((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl 4-nitrobenzoate
1435752-36-5

((1R,3R,5S)-5-acetoxy-3-(tert-butyldimethylsilyloxy)-2-methylenecyclopentyl)methyl 4-nitrobenzoate

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
2.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
2.2: 4.17 h / -10 °C / Inert atmosphere
3.1: formic acid / 9 h / 50 °C / Inert atmosphere
4.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
4.2: pH 7 / Inert atmosphere
View Scheme
((1R,3R,5S)-5-acetoxy-3-hydroxy-2-methylenecyclopentyl)methyl 4-nitrobenzoate
1435752-42-3

((1R,3R,5S)-5-acetoxy-3-hydroxy-2-methylenecyclopentyl)methyl 4-nitrobenzoate

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
1.2: 4.17 h / -10 °C / Inert atmosphere
2.1: formic acid / 9 h / 50 °C / Inert atmosphere
3.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
3.2: pH 7 / Inert atmosphere
View Scheme
((1R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate
1435752-48-9

((1R,3S,5S)-5-acetoxy-3-(2-amino-6-chloro-9H-purin-9-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: formic acid / 9 h / 50 °C / Inert atmosphere
2.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
2.2: pH 7 / Inert atmosphere
View Scheme
2-Amino-6-chloropurin
10310-21-1

2-Amino-6-chloropurin

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
1.2: 4.17 h / -10 °C / Inert atmosphere
2.1: formic acid / 9 h / 50 °C / Inert atmosphere
3.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
3.2: pH 7 / Inert atmosphere
View Scheme
((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate
1435752-55-8

((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Stage #1: ((1R,3S,5S)-5-acetoxy-3-(2-amino-6-oxo-1H-purin-9(6H)-yl)-2-methylenecyclopentyl)methyl 4-nitrobenzoate With sodium methylate In methanol at 20℃; for 0.5h; Inert atmosphere;
Stage #2: With hydrogenchloride; tert-butyl methyl ether In methanol pH=7; Inert atmosphere;
2.37 g
C10H20O2Si

C10H20O2Si

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: sodium acetate; dihydrogen peroxide / tetrahydrofuran; water / 0.83 h / 0 - 20 °C / Inert atmosphere
1.2: Enzymatic reaction
2.1: 1H-imidazole / tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere
3.1: potassium carbonate; methanol / 1 h / 20 °C / Inert atmosphere
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C / Inert atmosphere
5.1: triethylamine; dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
6.1: 2,4,6-trimethyl-pyridine; zinc; bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
7.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
8.1: [(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid; methanol / 4 h / 0 - 20 °C / Inert atmosphere; Enzymatic reaction
9.1: triphenylphosphine / tetrahydrofuran / 0.25 h / 20 °C / Inert atmosphere
9.2: 4.17 h / -10 °C / Inert atmosphere
10.1: formic acid / 9 h / 50 °C / Inert atmosphere
11.1: sodium methylate / methanol / 0.5 h / 20 °C / Inert atmosphere
11.2: pH 7 / Inert atmosphere
View Scheme
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

ω-chlorocaprylic acid
1795-62-6

ω-chlorocaprylic acid

N-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylene-cyclopentyl]-2-6H-purin-6-oneoctanamide

N-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylene-cyclopentyl]-2-6H-purin-6-oneoctanamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 30℃; for 8h;74%
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

N-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylene-cyclopentyl]-2-6H-purin-6-onelaurylamide

N-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylene-cyclopentyl]-2-6H-purin-6-onelaurylamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 50℃; for 8h;68%
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

Reaxys ID: 30033682

Reaxys ID: 30033682

Reaxys ID: 30033679

Reaxys ID: 30033679

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-1-isopropoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-1-isopropoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-1-cyclohexyloxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-1-cyclohexyloxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-((methoxycarbonylmethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-((methoxycarbonylmethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-((ethoxycarbonylmethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-((ethoxycarbonylmethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-((isopropoxycarbonylmethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-((isopropoxycarbonylmethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-1-ethoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-1-ethoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
View Scheme
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

A

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((R)-(1S)-1-ethoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((R)-(1S)-1-ethoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

B

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-(1S)-1-ethoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(((S)-(1S)-1-ethoxycarbonylethylamino(phenoxy)phosphoryl)oxymethyl)-2-methylidenecyclopentyl]-6H-purin-6-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
3: Diacel's Chiralpak AS / acetonitrile; ethanol
View Scheme
Multi-step reaction with 3 steps
1: N,N-dimethyl-formamide / 20 °C
2: 1-methyl-1H-imidazole / tetrahydrofuran / 20 °C
3: Diacel's Chiralpak AS / acetonitrile; isopropyl alcohol
View Scheme
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one
142217-69-4

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-metylidenecyclopentyl]-3H-purin-6-one

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

C15H20N6O3

C15H20N6O3

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃;

142217-69-4Downstream Products

142217-69-4Relevant articles and documents

A novel and efficient synthesis of Entecavir

Liu, Xiaoyu,Jiao, Xiaozhen,Wu, Qian,Tian, Chengsen,Li, Renze,Xie, Ping

, p. 3805 - 3807 (2012)

A practical synthesis of Entecavir (1) has been accomplished in 10 steps with 21% overall yield. The key steps to construct the five-membered carbocyclic framework 2 are a ring-closing metathesis and a diethyl-aluminum 2,2,6,6-tetramethyl piperidide (DA-TMS) mediated epoxide isomerization. Furthermore, the guanine was introduced by modified Mitsunobu reaction.

Novel preparation method and intermediates of entecavir

-

, (2021/04/10)

The invention provides novel intermediates used for entecavir synthesis, compounds shown as a formula II and a formula III in the description, and a novel method for synthesizing entecavir by using the novel intermediates. When the novel intermediates are used for synthesizing entecavir, not only can the synthesis yield be remarkably improved, but also the production cost can be reduced.

Entecavir intermediate, synthetic method thereof and synthetic method of entecavir

-

, (2020/07/29)

The invention belongs to the technical field of organic synthesis, and provides an entecavir intermediate, a synthesis method thereof and a method for synthesizing entecavir by using the entecavir intermediate. The intermediate and the methods have the advantages of easily available raw materials, low price, shortest synthesis steps, mild reaction conditions, easiness in control, simple equipmentrequirements, high total yield of products and easiness in industrial production.

Method for synthesizing entecavir

-

Paragraph 0040; 0060-0062; 0069, (2019/04/27)

The invention provides a method for synthesizing entecavir. The method comprises the steps of carrying out condensation ring-closure reaction, bromination addition reaction, reduction reaction, Witting reaction and the like. The method has the beneficial effects that the reaction raw material is easy to obtain, the reaction process is simple in operation, the requirement on reaction equipment is low, the reaction condition is relatively mild and the yield and the content are high.

Post a RFQ

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

1

What can I do for you?
Get Best Price

Get Best Price for 142217-69-4