2-Amino-9-((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-methylenecyclopentyl)-1H-purin-6(9H)-one

Name: 2-Amino-9-((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-methylenecyclopentyl)-1H-purin-6(9H)-one
Brand: ChemScene
Availability: InStock
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CAS No. 142217-81-0
Cat. No. CS-0158057
Purity≥97%
MDL No.None

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2-Amino-9-((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-methylenecyclopentyl)-1H-purin-6(9H)-one|CS-0158057

Structure of 142217-81-0

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General Information

CAS No. 142217-81-0
Cat. No. CS-0158057
Purity ≥97%
MDL No. None
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₆H₂₇N₅O₃
Molecular Weight 457.52
Synonym(s) The intermediate of Entecavir hydrate
SMILES O=C1NC(N)=NC2=C1N=CN2[C@@H]3C([C@H](COCC4=CC=CC=C4)[C@@H](OCC5=CC=CC=C5)C3)=C

Description

This purine derivative features a uniquely functionalized cyclopentyl scaffold bearing benzyl ether and methylene groups, enabling precise spatial control in nucleoside analog synthesis. The amino-purine core integrates readily into bioactive heterocycles, while the benzyloxy substituents provide orthogonal protection for downstream transformations under standard conditions.

Application

2-Amino-9-((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-methylenecyclopentyl)-1H-purin-6(9H)-one serves as a key purine scaffold for medicinal chemistry exploration, featuring orthogonal benzyl protecting groups that enable selective deprotection and functionalization. Its stable cyclopentyl core facilitates modular derivatization, while the amino and carbonyl functionalities support standard coupling and transformation protocols in nucleoside analog synthesis.

Synthesis

Route1
- 142217-80-9
- ~91%
- In-stock
  
  142217-81-0
References
- Bisacchi; Chao; Bachard; Daris; Innaimo; Jacobs; Kocy; Lapointe; Martel; Merchant; Slusarchyk; Sundeen; Young; Colonno; Zahler Bioorganic and Medicinal Chemistry Letters, 1997 , vol. 7, # 2 p. 127 - 132
Route2
- In-stock
  
  3587-60-8
- ~%
- In-stock
  
  142217-81-0
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 7, # 2 p. 127 - 132
Route3
- 39939-07-6
- ~%
- In-stock
  
  142217-81-0
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 7, # 2 p. 127 - 132

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 108.05
LogP 3.6212
H_Acceptors 7
H_Donors 2
Rotatable_Bonds 8

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic heterocycle compounds Purine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

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2-Amino-9-((1S,3R,4S)-4-(benzyloxy)-3-((benzyloxy)methyl)-2-methylenecyclopentyl)-1H-purin-6(9H)-one

CAS No. 142217-81-0

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