142217-81-0

Basic information

• Product Name: 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one
• Synonyms: 3',5'-Di-O-benzyl Entecavir;2-AMino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxyMethyl)-2-Methylenecyclopentyl]-6H-purin-6-one (interMediate 7);2-AMino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxyMethyl)-2-Methylenecyclopentyl]-6H-purin;2-Amino-9-((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)-methyl)-2-methylenecyclopentyl)-1H-purin-6(9H);6H-Purin-6-one,2-amino-1,9-dihydro-9[(1S,3R,4S)-2-methylene-4-(phenylmethoxy)-3-[([phenylmethoxy)methyl]cyclopentyl]-;N-1 Entecavir API;2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-p;Entecavir dibenzylated
• CAS NO: 142217-81-0
• Molecular Formula: C₂₆H₂₇N₅O₃
• Molecular Weight: 457.52
• EINECS: 1312995-182-4
• Mol File: 142217-81-0.mol

Chemical Properties

• Appearance: /
• Density: 1.34
• Refractive Index: 1.679
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly)
• PKA: 9?+-.0.20(Predicted)
• CAS DataBase Reference: 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one(142217-81-0)
• EPA Substance Registry System: 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one(142217-81-0)

Safety Data

• Hazardous Substances Data: 142217-81-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one is used as an intermediate in the synthesis of various pharmaceutical compounds. Its complex structure and functional groups make it a valuable building block for the development of new drugs targeting specific biological pathways.
Used in Antiviral Agents:
Specifically, 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one is used as an intermediate in the preparation of the hepatitis B antiviral agent, Entecavir (E558900). Entecavir is a nucleoside analog used for the treatment of chronic hepatitis B virus infection, and this compound plays a crucial role in its synthesis, contributing to its antiviral properties.
Chemical Properties:
The compound is described as a white powder, indicating its solid state at room temperature and typical appearance for many organic compounds. Its chemical properties, such as solubility and reactivity, would depend on the specific functional groups and stereochemistry present in its structure.

InChI:InChI=1/C26H27N5O3/c1-17-20(15-33-13-18-8-4-2-5-9-18)22(34-14-19-10-6-3-7-11-19)12-21(17)31-16-28-23-24(31)29-26(27)30-25(23)32/h2-11,16,20-22H,1,12-15H2,(H3,27,29,30,32)/t20-,21-,22-/m0/s1

Upstream product

• 142217-80-9 6-(benzyloxy)-9-((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-methylidenecyclopentyl)-N-((4-methoxyphenyl)diphenylmethyl)-9H-purin-2-amine 
• 3587-60-8 Benzyloxymethyl chloride 
• 39939-07-6 5-(benzyloxymethyl)cyclopentadiene 
• 110567-22-1 (2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane 
• 117641-39-1 (2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol 
• 110567-21-0 (1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene 
• 142217-78-5 (1S,2S,3S,5S)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-benzyloxy-9H-purin-9-yl]-3-benzyloxy-2-[(benzyloxy)methyl]cyclopentanol 
• 142217-79-6 (2R,3S,5S)-5-[2-[[(4-methoxyphenyl)diphenylmethyl]amino]-6-benzyloxy-9H-fluoren-9-yl]-3-benzyloxy-2-[(benzyloxy)methyl]cyclopentanone 
• 142217-77-4 [1S-(1α,2β,3α,5β)]-5-(2-amino-6-benzyloxy-9H-purin-9-yl)-3-benzyloxy-2-(benzyloxy)methyl-cyclopentanol 
• 4984-82-1 sodium cyclopentadienylide 
• 1354715-02-8 (1R,3R,4S)-4-benzyloxy-3-(benzyloxymethyl)-2-methylene-cyclopentanol 
• 100-52-7 benzaldehyde 
• 256390-84-8 (S)-4-(hydroxymethyl)-2-phenyl-1,3-dioxane 
• 139884-80-3 1,3-O-benzylidene-1,3-dihydroxy-4(Z)-pentane 

Downstream Products

• 142217-69-4 entecavir 

Relevant articles and documents

Improved entecavir intermediate synthesis process and improved entecavir synthesis process

The invention discloses an improved entecavir intermediate synthesis process and an improved entecavir synthesis process, and relates to the technical field of drug synthesis. The invention disclosesan improved entecavir intermediate synthesis process. In the synthesis process of an amino protection reaction product, amino protecting groups are added in batches; and the ratio of the reaction rawmaterials is optimized, so that the problems of long reaction time and relatively low amino protection reaction yield due to adoption of a one-time complete feeding mode in an existing synthesis modeare solved, the synthesis time of an amino protection reaction product is shortened to 50-70 minutes, and the obtained product is high in yield and purity. According to the improved entecavir synthesis process, in the amino protection reaction product synthesis process, reaction conditions are effectively optimized, and the purity of obtained entecavir reaches 99% or above.

Entecavir preparation method using Boc protection group

The invention belongs to the field of drug synthesis, and provides an entecavir preparation method using a Boc protection group, wherein particularly a compound represented by a formula III is prepared in a high yield manner by carrying out a reaction on a compound represented by a formula II and having a Boc group and a compound represented by a formula I, and the total yield of the subsequent oxidation, the methyleneation and the protection group removal is further improved so as to integrally improve the synthesis yield of entecavir, such that the method is suitable for industrial large-scale production. The formulas I, II and III are defined in the specification.

A method for preparation of a purine derivative and intermediates

The invention discloses a preparation method and intermediates of purine derivatives. According to the preparation method, a compound II and a compound III have a coupling reaction in an organic solvent under the actions of alkali and palladium catalysts to prepare the purine derivatives. Compared with the prior art, the raw materials used in the preparation method are cheap and common, and the preparation method is simple and efficient, is suitable for industrial production and provides a new way for the synthesis of entecavir drugs.

BMS-200475, a novel carbocyclic 2'-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro

BMS-200475, a never carbocyclic analog of 2'-deoxyguanosine, is a potent inhibitor of hepatitis B virus in vitro (ED50 = 3 nM) with relatively low cytotoxicity (CC50 = 21-120 μM). A practical 10-step asymmetric synthesis was developed affording BMS-200475 in 18% overall chemical yield and > 99% optical purity. The enantiomer of BMS-200475 as well as the adenine, thymine, and iodouracil analogs are much less active.

Hydroxymethyl (methylenecyclopentyl) purines and pyrimidines

Antiviral activity is exhibited by compounds having the formula STR1 and its pharmaceutically acceptable salts.