24587-86-8

Usage

Uses

Used in Pharmaceutical Industry:
[6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methanol is used as a potential pharmaceutical compound for its unique structure and properties. [6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methanol's ability to interact with biological systems and its potential to be modified for specific applications make it a promising candidate for drug development.
Used in Organic Synthesis:
In the field of organic synthesis, [6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methanol can be used as a building block or intermediate for the synthesis of more complex molecules. Its unique structure may allow for the creation of novel compounds with specific properties and applications in various industries.

Upstream product

• 111189-93-6 {9-[(1R,4S)-4-(Benzenesulfonyl-nitro-methyl)-cyclopent-2-enyl]-9H-purin-6-yl}-carbamic acid methyl ester 
• 39939-07-6 5-(benzyloxymethyl)cyclopentadiene 
• 100021-19-0 (+/-)-(1β,2α,3β,4α,5α)-4,5-(dimethylmethylenedioxy)-2-hydroxy-3-<(phenylmethoxy)methyl>-1-cyclopentanamine 
• 66224-66-6 adenine 
• 74202-21-4 (1R,2R,6S,7R)-4,4-Dimethyl-9-trichloromethyl-3,5-dioxa-8-aza-tricyclo[5.2.1.0^2,6]decane-8-carboxylic acid ethyl ester 
• 100021-24-7 (+/-)-(1β,2α,3α,4β)-1-(6-amino-9H-purin-9-yl)-2,3-(dimethylmethylenedioxy)-4-<(phenylmethoxy)methyl>cyclopentane 
• 111189-94-7 {9-[(3aR,4R,6S,6aS)-6-(Benzenesulfonyl-nitro-methyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-yl}-carbamic acid methyl ester 
• 111189-95-8 9-[(3aR,4R,6S,6aS)-6-(Benzenesulfonyl-nitro-methyl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-9H-purin-6-ylamine 
• 111189-92-5 Carbonic acid (1R,4S)-4-(6-methoxycarbonylamino-purin-9-yl)-cyclopent-2-enyl ester methyl ester 
• 111189-91-4 (1R,4S)-4-(6-Amino-purin-9-yl)-cyclopent-2-enol 
• 7129-41-1 6-oxabicyclo<3.1.0>hex-2-ene 
• 111265-84-0 (3aR,4R,6S,6aS)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxole-4-carboxylic acid methyl ester 
• 74212-23-0 ((3aR,4S,6S,6aS)-2,2-Dimethyl-6-vinyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-carbamic acid ethyl ester 
• 100021-16-7 (+/-)-(1α,2β,3α,4α,5β)-2-azido-3,4-(dimethylmethylenedioxy)-5-<(phenylmethoxy)methyl>-1-cyclopentanol 

Downstream Products

• 72346-00-0 (+/-)-9-<2α,3α-dihydroxy-4α-(hydroxymethyl)cyclopent-1α-yl>adenine 

Relevant academic research and scientific papers

Synthetic Studies towards (±)-Aristeromycin and its 5′-homo-Analogue

A new synthetic pathway to the carbocyclic nucleoside analogues (±)-aristeromycin (15) and its 5′-homo-derivative (17) has been developed starting form norborn-5-en-2-one using nucleophilic substitution of a sulfonate ester group by the aglycone.

A Novel and Stereospecific Synthesis of (+/-)- and (-)-Aristeromycin

A new, efficient synthetic route to (+/-)- and (-)-aristeromycin (1) has been developed which has as its key feature the cycloaddition of singlet oxygen to 5--1,3-cyclopentadiene (8) followed by in situ reduction to give ene diol 10.This reaction has been optimized and scaled-up to give 197 g (60percent) of partially purified 10.The key intermediate azide 15 was prepared from the partially purified 10 in 56percent yield by a three-step sequence of epoxidation to give 13, reaction with NaN3, and acetonation.Azide 15 was converted by standard chemistry via adenine intermediate 22 to (+/-)-aristeromycin (1) in 31percent overall yield.Intermediate 22 was also prepared in 25percent yield by a novel and shorter sequence which involved the reaction of epoxide 13 with the sodium salt of adenine and then acetonation.Alternatively, azide 15 was resolved by conversion to its naproxen ester 26, and the (-)-isomer of 15 was converted to the known amino triol 31, thus constituting a formal synthesis of (-)-aristeromycin.

A CONVENIENT ROUTE TO CARBOCYCLIC ANALOGS OF NUCLEOSIDES: (+/-) ARISTEROMYCIN

Stereocontrolled elaboration of cyclopentadien-azomethine adducts 1 and 2 led to a short total synthesis of (+/-) aristeromycin.In the course of this work a novel zinc reduction was observed.Also, ozonolysis of the gem-dihalo olefin 10 in metha