Improved access to 2- O-monobenzyl ethers of β-cyclodextrin as precursors of catalysts for organophosphoryl esters hydrolysis

A comparative study of reaction conditions was performed for the synthesis of a 2- O-monobenzyl ether of cyclomaltoheptaose (β-CD). Optimal conditions involved sodium ethoxide in Me 2SO and benzyl bromide. The methodology was extended to the preparation of various 2 I- O-iodobenzyl and 2 I- O-carbox...

Full description

Saved in:
Bibliographic Details
Published in:Carbohydrate research 2006-05, Vol.341 (7), p.935-940
Main Authors: Masurier, Nicolas, Estour, François, Lefèvre, Bertrand, Brasme, Bernard, Masson, Patrick, Lafont, Olivier
Format: Article
Language:English
Subjects:
Benzyl ethers
beta-Cyclodextrins - chemistry
Catalysis
Catalysts
Chemical Sciences
Enzyme mimics
Esters - metabolism
Ethanol - analogs & derivatives
Ethanol - chemistry
Ethers - chemical synthesis
Ethers - chemistry
Hydrolysis
Life Sciences
Organophosphoryl esters
Paraoxon - metabolism
β-Cyclodextrin monosubstitution
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c394t-92fb0e038a1b11e826aa128f14095b2223ff40fbd7729bc993ee9a1fd6c3fa0d3
cites cdi_FETCH-LOGICAL-c394t-92fb0e038a1b11e826aa128f14095b2223ff40fbd7729bc993ee9a1fd6c3fa0d3
container_end_page 940
container_issue 7
container_start_page 935
container_title Carbohydrate research
container_volume 341
creator Masurier, Nicolas
Estour, François
Lefèvre, Bertrand
Brasme, Bernard
Masson, Patrick
Lafont, Olivier
description A comparative study of reaction conditions was performed for the synthesis of a 2- O-monobenzyl ether of cyclomaltoheptaose (β-CD). Optimal conditions involved sodium ethoxide in Me 2SO and benzyl bromide. The methodology was extended to the preparation of various 2 I- O-iodobenzyl and 2 I- O-carboxymethylbenzyl derivatives of β-CD including a 3-carboxymethyl-4-iodobenzyl derivative of interest as precursor of an enzyme mimic to degrade the organophosphoryl ester diethyl 4-nitrophenyl phosphate (paraoxon).
doi_str_mv 10.1016/j.carres.2006.02.012
format article
fullrecord <record><control><sourceid>pubmed_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_02375831v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0008621506000711</els_id><sourcerecordid>16530173</sourcerecordid><originalsourceid>FETCH-LOGICAL-c394t-92fb0e038a1b11e826aa128f14095b2223ff40fbd7729bc993ee9a1fd6c3fa0d3</originalsourceid><addsrcrecordid>eNp9kMtq3DAUhkVpaCaXNyhF2y7sHEke2d4EQmguMJBNCt0JWTrqePBYRnKGuIs8VB6kzxQZh2bXhTjo8P2_0EfIVwY5AyYvdrnRIWDMOYDMgefA-CeyYlUpsoLLX5_JCgCqTHK2PiYnMe7SFWQpv5BjJtcCWClW5OV-PwR_QEu1MRgjHT3lGX3I9r73DfZ_po7iuMUQqXf072tmJtN5i89jaHuqIx0CmqcQ_QIYPepuimOkzgfqw2_d-2HrYzphborj3LSdbPAJa-MZOXK6i3j-Pk_Jz5sfj9d32ebh9v76apMZURdjVnPXAIKoNGsYw4pLrRmvHCugXjecc-FcAa6xZcnrxtS1QKw1c1Ya4TRYcUq-L71b3akhtHsdJuV1q-6uNmreARfluhLswBJbLKwJPsaA7l-AgZrVq51a1KtZfYqqpD7Fvi2x4anZo_0IvbtOwOUCYProocWgommxN2jb5HBU1rf_f-EN7P6aSg</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Improved access to 2- O-monobenzyl ethers of β-cyclodextrin as precursors of catalysts for organophosphoryl esters hydrolysis</title><source>ScienceDirect Freedom Collection</source><creator>Masurier, Nicolas ; Estour, François ; Lefèvre, Bertrand ; Brasme, Bernard ; Masson, Patrick ; Lafont, Olivier</creator><creatorcontrib>Masurier, Nicolas ; Estour, François ; Lefèvre, Bertrand ; Brasme, Bernard ; Masson, Patrick ; Lafont, Olivier</creatorcontrib><description>A comparative study of reaction conditions was performed for the synthesis of a 2- O-monobenzyl ether of cyclomaltoheptaose (β-CD). Optimal conditions involved sodium ethoxide in Me 2SO and benzyl bromide. The methodology was extended to the preparation of various 2 I- O-iodobenzyl and 2 I- O-carboxymethylbenzyl derivatives of β-CD including a 3-carboxymethyl-4-iodobenzyl derivative of interest as precursor of an enzyme mimic to degrade the organophosphoryl ester diethyl 4-nitrophenyl phosphate (paraoxon).</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>EISSN: 0008-6215</identifier><identifier>DOI: 10.1016/j.carres.2006.02.012</identifier><identifier>PMID: 16530173</identifier><language>eng</language><publisher>Netherlands: Elsevier Ltd</publisher><subject>Benzyl ethers ; beta-Cyclodextrins - chemistry ; Catalysis ; Catalysts ; Chemical Sciences ; Enzyme mimics ; Esters - metabolism ; Ethanol - analogs &amp; derivatives ; Ethanol - chemistry ; Ethers - chemical synthesis ; Ethers - chemistry ; Hydrolysis ; Life Sciences ; Organophosphoryl esters ; Paraoxon - metabolism ; β-Cyclodextrin monosubstitution</subject><ispartof>Carbohydrate research, 2006-05, Vol.341 (7), p.935-940</ispartof><rights>2006 Elsevier Ltd</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c394t-92fb0e038a1b11e826aa128f14095b2223ff40fbd7729bc993ee9a1fd6c3fa0d3</citedby><cites>FETCH-LOGICAL-c394t-92fb0e038a1b11e826aa128f14095b2223ff40fbd7729bc993ee9a1fd6c3fa0d3</cites><orcidid>0000-0001-9169-8149 ; 0000-0002-6304-8920</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16530173$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://normandie-univ.hal.science/hal-02375831$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Masurier, Nicolas</creatorcontrib><creatorcontrib>Estour, François</creatorcontrib><creatorcontrib>Lefèvre, Bertrand</creatorcontrib><creatorcontrib>Brasme, Bernard</creatorcontrib><creatorcontrib>Masson, Patrick</creatorcontrib><creatorcontrib>Lafont, Olivier</creatorcontrib><title>Improved access to 2- O-monobenzyl ethers of β-cyclodextrin as precursors of catalysts for organophosphoryl esters hydrolysis</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>A comparative study of reaction conditions was performed for the synthesis of a 2- O-monobenzyl ether of cyclomaltoheptaose (β-CD). Optimal conditions involved sodium ethoxide in Me 2SO and benzyl bromide. The methodology was extended to the preparation of various 2 I- O-iodobenzyl and 2 I- O-carboxymethylbenzyl derivatives of β-CD including a 3-carboxymethyl-4-iodobenzyl derivative of interest as precursor of an enzyme mimic to degrade the organophosphoryl ester diethyl 4-nitrophenyl phosphate (paraoxon).</description><subject>Benzyl ethers</subject><subject>beta-Cyclodextrins - chemistry</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical Sciences</subject><subject>Enzyme mimics</subject><subject>Esters - metabolism</subject><subject>Ethanol - analogs &amp; derivatives</subject><subject>Ethanol - chemistry</subject><subject>Ethers - chemical synthesis</subject><subject>Ethers - chemistry</subject><subject>Hydrolysis</subject><subject>Life Sciences</subject><subject>Organophosphoryl esters</subject><subject>Paraoxon - metabolism</subject><subject>β-Cyclodextrin monosubstitution</subject><issn>0008-6215</issn><issn>1873-426X</issn><issn>0008-6215</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNp9kMtq3DAUhkVpaCaXNyhF2y7sHEke2d4EQmguMJBNCt0JWTrqePBYRnKGuIs8VB6kzxQZh2bXhTjo8P2_0EfIVwY5AyYvdrnRIWDMOYDMgefA-CeyYlUpsoLLX5_JCgCqTHK2PiYnMe7SFWQpv5BjJtcCWClW5OV-PwR_QEu1MRgjHT3lGX3I9r73DfZ_po7iuMUQqXf072tmJtN5i89jaHuqIx0CmqcQ_QIYPepuimOkzgfqw2_d-2HrYzphborj3LSdbPAJa-MZOXK6i3j-Pk_Jz5sfj9d32ebh9v76apMZURdjVnPXAIKoNGsYw4pLrRmvHCugXjecc-FcAa6xZcnrxtS1QKw1c1Ya4TRYcUq-L71b3akhtHsdJuV1q-6uNmreARfluhLswBJbLKwJPsaA7l-AgZrVq51a1KtZfYqqpD7Fvi2x4anZo_0IvbtOwOUCYProocWgommxN2jb5HBU1rf_f-EN7P6aSg</recordid><startdate>20060522</startdate><enddate>20060522</enddate><creator>Masurier, Nicolas</creator><creator>Estour, François</creator><creator>Lefèvre, Bertrand</creator><creator>Brasme, Bernard</creator><creator>Masson, Patrick</creator><creator>Lafont, Olivier</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0001-9169-8149</orcidid><orcidid>https://orcid.org/0000-0002-6304-8920</orcidid></search><sort><creationdate>20060522</creationdate><title>Improved access to 2- O-monobenzyl ethers of β-cyclodextrin as precursors of catalysts for organophosphoryl esters hydrolysis</title><author>Masurier, Nicolas ; Estour, François ; Lefèvre, Bertrand ; Brasme, Bernard ; Masson, Patrick ; Lafont, Olivier</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c394t-92fb0e038a1b11e826aa128f14095b2223ff40fbd7729bc993ee9a1fd6c3fa0d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Benzyl ethers</topic><topic>beta-Cyclodextrins - chemistry</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical Sciences</topic><topic>Enzyme mimics</topic><topic>Esters - metabolism</topic><topic>Ethanol - analogs &amp; derivatives</topic><topic>Ethanol - chemistry</topic><topic>Ethers - chemical synthesis</topic><topic>Ethers - chemistry</topic><topic>Hydrolysis</topic><topic>Life Sciences</topic><topic>Organophosphoryl esters</topic><topic>Paraoxon - metabolism</topic><topic>β-Cyclodextrin monosubstitution</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Masurier, Nicolas</creatorcontrib><creatorcontrib>Estour, François</creatorcontrib><creatorcontrib>Lefèvre, Bertrand</creatorcontrib><creatorcontrib>Brasme, Bernard</creatorcontrib><creatorcontrib>Masson, Patrick</creatorcontrib><creatorcontrib>Lafont, Olivier</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Masurier, Nicolas</au><au>Estour, François</au><au>Lefèvre, Bertrand</au><au>Brasme, Bernard</au><au>Masson, Patrick</au><au>Lafont, Olivier</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Improved access to 2- O-monobenzyl ethers of β-cyclodextrin as precursors of catalysts for organophosphoryl esters hydrolysis</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>2006-05-22</date><risdate>2006</risdate><volume>341</volume><issue>7</issue><spage>935</spage><epage>940</epage><pages>935-940</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><eissn>0008-6215</eissn><abstract>A comparative study of reaction conditions was performed for the synthesis of a 2- O-monobenzyl ether of cyclomaltoheptaose (β-CD). Optimal conditions involved sodium ethoxide in Me 2SO and benzyl bromide. The methodology was extended to the preparation of various 2 I- O-iodobenzyl and 2 I- O-carboxymethylbenzyl derivatives of β-CD including a 3-carboxymethyl-4-iodobenzyl derivative of interest as precursor of an enzyme mimic to degrade the organophosphoryl ester diethyl 4-nitrophenyl phosphate (paraoxon).</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>16530173</pmid><doi>10.1016/j.carres.2006.02.012</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-9169-8149</orcidid><orcidid>https://orcid.org/0000-0002-6304-8920</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0008-6215
ispartof Carbohydrate research, 2006-05, Vol.341 (7), p.935-940
issn 0008-6215
1873-426X
0008-6215
language eng
recordid cdi_hal_primary_oai_HAL_hal_02375831v1
source ScienceDirect Freedom Collection
subjects Benzyl ethers
beta-Cyclodextrins - chemistry
Catalysis
Catalysts
Chemical Sciences
Enzyme mimics
Esters - metabolism
Ethanol - analogs & derivatives
Ethanol - chemistry
Ethers - chemical synthesis
Ethers - chemistry
Hydrolysis
Life Sciences
Organophosphoryl esters
Paraoxon - metabolism
β-Cyclodextrin monosubstitution
title Improved access to 2- O-monobenzyl ethers of β-cyclodextrin as precursors of catalysts for organophosphoryl esters hydrolysis
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T04%3A52%3A05IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pubmed_hal_p&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Improved%20access%20to%202-%20O-monobenzyl%20ethers%20of%20%CE%B2-cyclodextrin%20as%20precursors%20of%20catalysts%20for%20organophosphoryl%20esters%20hydrolysis&rft.jtitle=Carbohydrate%20research&rft.au=Masurier,%20Nicolas&rft.date=2006-05-22&rft.volume=341&rft.issue=7&rft.spage=935&rft.epage=940&rft.pages=935-940&rft.issn=0008-6215&rft.eissn=1873-426X&rft_id=info:doi/10.1016/j.carres.2006.02.012&rft_dat=%3Cpubmed_hal_p%3E16530173%3C/pubmed_hal_p%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c394t-92fb0e038a1b11e826aa128f14095b2223ff40fbd7729bc993ee9a1fd6c3fa0d3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/16530173&rfr_iscdi=true