A Convenient and Chemoselective One-Pot Oxidation/Wittig Reaction for the C2-Homologation of Carbohydrate-Derived Glycols

A simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2005-11, Vol.70 (24), p.10099-10101
Main Authors: Pinacho Crisóstomo, Fernando R, Carrillo, Romen, Martín, Tomás, García-Tellado, Fernando, Martín, Víctor S
Format: Article
Language:English
Subjects:
Carbohydrates - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Glycols - chemical synthesis
Glycols - chemistry
Molecular Conformation
Organic chemistry
Oxidation-Reduction
Preparations and properties
Stereoisomerism
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites
container_end_page 10101
container_issue 24
container_start_page 10099
container_title Journal of organic chemistry
container_volume 70
creator Pinacho Crisóstomo, Fernando R
Carrillo, Romen
Martín, Tomás
García-Tellado, Fernando
Martín, Víctor S
description A simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not need selective protective group manipulation, and it is safe, economical, fast (5 to 6 h), and bench-friendly. Its general utility is discussed.
doi_str_mv 10.1021/jo051566e
format article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_68809442</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>68809442</sourcerecordid><originalsourceid>FETCH-LOGICAL-a323e-96fd7c22b060eed2a6f34ef220404d1f04f449a6d711212b1dc38c4781b46b513</originalsourceid><addsrcrecordid>eNpF0U1v1DAQBmALgehSOPAHkC9wC_V3kmOV0g-10lawqEfLscddL0lcbG_V_fdN6dLOZTSaR-9hBqHPlHynhNGjTSSSSqXgDVpQyUilWiLeogUhjFWcKX6APuS8IXNJKd-jA6pYyxqhFmh3jLs43cMUYCrYTA53axhjhgFsCfeAlxNU17Hg5UNwpoQ4Hd2EUsIt_gnGPs3Yx4TLGnDHqvM4xiHe_nM4etyZ1Mf1ziVToDqBNAc6fDbsbBzyR_TOmyHDp30_RL9Pf6y68-pqeXbRHV9VhjMOVau8qy1jPVEEwDGjPBfgGSOCCEc9EV6I1ihXU8oo66mzvLGibmgvVC8pP0TfnnPvUvy7hVz0GLKFYTATxG3WqmlIKwSb4Zc93PYjOH2XwmjSTv8_1gy-7oHJ1gw-mcmG_OpqTrki7eyqZxdygYeXvUl_tKp5LfXq-pe-6U4u1epS6tPXXGOz3sRtmuZ7aEr003P1y3P5I3r4kt4</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68809442</pqid></control><display><type>article</type><title>A Convenient and Chemoselective One-Pot Oxidation/Wittig Reaction for the C2-Homologation of Carbohydrate-Derived Glycols</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Pinacho Crisóstomo, Fernando R ; Carrillo, Romen ; Martín, Tomás ; García-Tellado, Fernando ; Martín, Víctor S</creator><creatorcontrib>Pinacho Crisóstomo, Fernando R ; Carrillo, Romen ; Martín, Tomás ; García-Tellado, Fernando ; Martín, Víctor S</creatorcontrib><description>A simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not need selective protective group manipulation, and it is safe, economical, fast (5 to 6 h), and bench-friendly. Its general utility is discussed.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo051566e</identifier><identifier>PMID: 16292846</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Carbohydrates - chemistry ; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; Exact sciences and technology ; Glycols - chemical synthesis ; Glycols - chemistry ; Molecular Conformation ; Organic chemistry ; Oxidation-Reduction ; Preparations and properties ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2005-11, Vol.70 (24), p.10099-10101</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=17313609$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16292846$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pinacho Crisóstomo, Fernando R</creatorcontrib><creatorcontrib>Carrillo, Romen</creatorcontrib><creatorcontrib>Martín, Tomás</creatorcontrib><creatorcontrib>García-Tellado, Fernando</creatorcontrib><creatorcontrib>Martín, Víctor S</creatorcontrib><title>A Convenient and Chemoselective One-Pot Oxidation/Wittig Reaction for the C2-Homologation of Carbohydrate-Derived Glycols</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>A simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not need selective protective group manipulation, and it is safe, economical, fast (5 to 6 h), and bench-friendly. Its general utility is discussed.</description><subject>Carbohydrates - chemistry</subject><subject>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Glycols - chemical synthesis</subject><subject>Glycols - chemistry</subject><subject>Molecular Conformation</subject><subject>Organic chemistry</subject><subject>Oxidation-Reduction</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><recordid>eNpF0U1v1DAQBmALgehSOPAHkC9wC_V3kmOV0g-10lawqEfLscddL0lcbG_V_fdN6dLOZTSaR-9hBqHPlHynhNGjTSSSSqXgDVpQyUilWiLeogUhjFWcKX6APuS8IXNJKd-jA6pYyxqhFmh3jLs43cMUYCrYTA53axhjhgFsCfeAlxNU17Hg5UNwpoQ4Hd2EUsIt_gnGPs3Yx4TLGnDHqvM4xiHe_nM4etyZ1Mf1ziVToDqBNAc6fDbsbBzyR_TOmyHDp30_RL9Pf6y68-pqeXbRHV9VhjMOVau8qy1jPVEEwDGjPBfgGSOCCEc9EV6I1ihXU8oo66mzvLGibmgvVC8pP0TfnnPvUvy7hVz0GLKFYTATxG3WqmlIKwSb4Zc93PYjOH2XwmjSTv8_1gy-7oHJ1gw-mcmG_OpqTrki7eyqZxdygYeXvUl_tKp5LfXq-pe-6U4u1epS6tPXXGOz3sRtmuZ7aEr003P1y3P5I3r4kt4</recordid><startdate>20051125</startdate><enddate>20051125</enddate><creator>Pinacho Crisóstomo, Fernando R</creator><creator>Carrillo, Romen</creator><creator>Martín, Tomás</creator><creator>García-Tellado, Fernando</creator><creator>Martín, Víctor S</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20051125</creationdate><title>A Convenient and Chemoselective One-Pot Oxidation/Wittig Reaction for the C2-Homologation of Carbohydrate-Derived Glycols</title><author>Pinacho Crisóstomo, Fernando R ; Carrillo, Romen ; Martín, Tomás ; García-Tellado, Fernando ; Martín, Víctor S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a323e-96fd7c22b060eed2a6f34ef220404d1f04f449a6d711212b1dc38c4781b46b513</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Carbohydrates - chemistry</topic><topic>Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Glycols - chemical synthesis</topic><topic>Glycols - chemistry</topic><topic>Molecular Conformation</topic><topic>Organic chemistry</topic><topic>Oxidation-Reduction</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pinacho Crisóstomo, Fernando R</creatorcontrib><creatorcontrib>Carrillo, Romen</creatorcontrib><creatorcontrib>Martín, Tomás</creatorcontrib><creatorcontrib>García-Tellado, Fernando</creatorcontrib><creatorcontrib>Martín, Víctor S</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pinacho Crisóstomo, Fernando R</au><au>Carrillo, Romen</au><au>Martín, Tomás</au><au>García-Tellado, Fernando</au><au>Martín, Víctor S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Convenient and Chemoselective One-Pot Oxidation/Wittig Reaction for the C2-Homologation of Carbohydrate-Derived Glycols</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-11-25</date><risdate>2005</risdate><volume>70</volume><issue>24</issue><spage>10099</spage><epage>10101</epage><pages>10099-10101</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>A simple and convenient one-pot protocol for the chemoselective C2-homologation of carbohydrate-derived glycols is described. The method comprises the chemoselective oxidation of the glycol to the corresponding hydroxyaldehyde and the subsequent Wittig alkenylation. In addition, the method does not need selective protective group manipulation, and it is safe, economical, fast (5 to 6 h), and bench-friendly. Its general utility is discussed.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16292846</pmid><doi>10.1021/jo051566e</doi><tpages>3</tpages><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2005-11, Vol.70 (24), p.10099-10101
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_68809442
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Carbohydrates - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Glycols - chemical synthesis
Glycols - chemistry
Molecular Conformation
Organic chemistry
Oxidation-Reduction
Preparations and properties
Stereoisomerism
title A Convenient and Chemoselective One-Pot Oxidation/Wittig Reaction for the C2-Homologation of Carbohydrate-Derived Glycols
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-08T03%3A12%3A46IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Convenient%20and%20Chemoselective%20One-Pot%20Oxidation/Wittig%20Reaction%20for%20the%20C2-Homologation%20of%20Carbohydrate-Derived%20Glycols&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Pinacho%20Cris%C3%B3stomo,%20Fernando%20R&rft.date=2005-11-25&rft.volume=70&rft.issue=24&rft.spage=10099&rft.epage=10101&rft.pages=10099-10101&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo051566e&rft_dat=%3Cproquest_pubme%3E68809442%3C/proquest_pubme%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a323e-96fd7c22b060eed2a6f34ef220404d1f04f449a6d711212b1dc38c4781b46b513%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=68809442&rft_id=info:pmid/16292846&rfr_iscdi=true