Loading…

1,3-Dipolar Cycloaddition Reaction of d-Glucose-Derived Nitrone with Allyl Alcohol: Synthesis of 2-Hydroxy-1-deoxycastanospermine Analogues

The synthesis and evaluation of glycosidase inhibitory activity of polyhydroxylated indolizidine alkaloids namely 2-hydroxy-1-deoxycastanospermine 3a,b and 2-hydroxy-1-deoxy-8a-epi-castanospermine 3c,d is reported. The key step involves the intermolecular 1,3-dipolar cycloaddition of allyl alcohol t...

Full description

Saved in:

Bibliographic Details
Published in:	Journal of organic chemistry 2005-02, Vol.70 (4), p.1356-1363
Main Authors:	Karanjule, Narayan S, Markad, Shankar D, Sharma, Tarun, Sabharwal, Sushma G, Puranik, Vedavati G, Dhavale, Dilip D
Format:	Article
Language:	English
Subjects:	Chemistry Exact sciences and technology Glucose - chemistry Glycoside Hydrolases - antagonists & inhibitors Glycoside Hydrolases - metabolism Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indolizines Inhibitory Concentration 50 Molecular Conformation Molecular Structure Nitrogen Oxides - chemistry Organic chemistry Preparations and properties Propanols - chemistry Stereoisomerism
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-a381t-8048caa1d8f0d539e15cf1bff9f9fdbc711569b8aa13f92391610528ec3f1ffc3
cites	cdi_FETCH-LOGICAL-a381t-8048caa1d8f0d539e15cf1bff9f9fdbc711569b8aa13f92391610528ec3f1ffc3
container_end_page	1363
container_issue	4
container_start_page	1356
container_title	Journal of organic chemistry
container_volume	70
creator	Karanjule, Narayan S Markad, Shankar D Sharma, Tarun Sabharwal, Sushma G Puranik, Vedavati G Dhavale, Dilip D
description	The synthesis and evaluation of glycosidase inhibitory activity of polyhydroxylated indolizidine alkaloids namely 2-hydroxy-1-deoxycastanospermine 3a,b and 2-hydroxy-1-deoxy-8a-epi-castanospermine 3c,d is reported. The key step involves the intermolecular 1,3-dipolar cycloaddition of allyl alcohol to d-glucose-derived nitrone 4, followed by tosylation, that afforded four diastereomeric sugar-substituted isoxazolidines 5a−d with the desired regioselectivity. The one-pot conversion of 5a−d to pyrrolidines 8a−d by hydrogenolysis, removal of 1,2-acetonoide functionality, and hydrogenation afforded corresponding target molecules 3a−d.
doi_str_mv	10.1021/jo048176x
format	article
fullrecord	<record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_jo048176x</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c589241209</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-8048caa1d8f0d539e15cf1bff9f9fdbc711569b8aa13f92391610528ec3f1ffc3</originalsourceid><addsrcrecordid>eNptkM1OGzEUha2KqgTaRV8AzYYFEi6-49gzwy4Kf5VCSwldjxz_EIMzjuwJZHZs2fQh-yR1SEQ2vZbuseTvHl0fhL4C-QYkh5MHT_olFHz5AfWA5QTzivR3UI-QPMc053QX7cX4QFIxxj6hXWAF6VcF6aE_cEzxmZ17J0I27KTzQinbWt9kt1rIt4s3mcKXbiF91PhMB_ukVfbDtsE3Onu27TQbONe51KWfenf69-U1G3dNO9XRxtV0jq86Ffyyw4CVTipFbEXj41yHmU0mg0Y4f7_Q8TP6aISL-stG99Hvi_O74RUe_bz8PhyMsKAltLhM_5VCgCoNUYxWGpg0MDGmSkdNZAHAeDUpE0JNldMKOBCWl1pSA8ZIuo-O1r4y-BiDNvU82JkIXQ2kXmVav2ea2IM1O19MZlptyU2ICTjcACJK4UwQjbRxy3FGS8Z54vCas7HVy_d3ER5rXtCC1Xc34_oXuRmOr2_79fXWV8iY9lmElFL8z4L_ABdsnPE</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>1,3-Dipolar Cycloaddition Reaction of d-Glucose-Derived Nitrone with Allyl Alcohol: Synthesis of 2-Hydroxy-1-deoxycastanospermine Analogues</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)</source><creator>Karanjule, Narayan S ; Markad, Shankar D ; Sharma, Tarun ; Sabharwal, Sushma G ; Puranik, Vedavati G ; Dhavale, Dilip D</creator><creatorcontrib>Karanjule, Narayan S ; Markad, Shankar D ; Sharma, Tarun ; Sabharwal, Sushma G ; Puranik, Vedavati G ; Dhavale, Dilip D</creatorcontrib><description>The synthesis and evaluation of glycosidase inhibitory activity of polyhydroxylated indolizidine alkaloids namely 2-hydroxy-1-deoxycastanospermine 3a,b and 2-hydroxy-1-deoxy-8a-epi-castanospermine 3c,d is reported. The key step involves the intermolecular 1,3-dipolar cycloaddition of allyl alcohol to d-glucose-derived nitrone 4, followed by tosylation, that afforded four diastereomeric sugar-substituted isoxazolidines 5a−d with the desired regioselectivity. The one-pot conversion of 5a−d to pyrrolidines 8a−d by hydrogenolysis, removal of 1,2-acetonoide functionality, and hydrogenation afforded corresponding target molecules 3a−d.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo048176x</identifier><identifier>PMID: 15704970</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Chemistry ; Exact sciences and technology ; Glucose - chemistry ; Glycoside Hydrolases - antagonists & inhibitors ; Glycoside Hydrolases - metabolism ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Indolizines ; Inhibitory Concentration 50 ; Molecular Conformation ; Molecular Structure ; Nitrogen Oxides - chemistry ; Organic chemistry ; Preparations and properties ; Propanols - chemistry ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2005-02, Vol.70 (4), p.1356-1363</ispartof><rights>Copyright © 2005 American Chemical Society</rights><rights>2005 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-8048caa1d8f0d539e15cf1bff9f9fdbc711569b8aa13f92391610528ec3f1ffc3</citedby><cites>FETCH-LOGICAL-a381t-8048caa1d8f0d539e15cf1bff9f9fdbc711569b8aa13f92391610528ec3f1ffc3</cites></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&idt=16538566$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15704970$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Karanjule, Narayan S</creatorcontrib><creatorcontrib>Markad, Shankar D</creatorcontrib><creatorcontrib>Sharma, Tarun</creatorcontrib><creatorcontrib>Sabharwal, Sushma G</creatorcontrib><creatorcontrib>Puranik, Vedavati G</creatorcontrib><creatorcontrib>Dhavale, Dilip D</creatorcontrib><title>1,3-Dipolar Cycloaddition Reaction of d-Glucose-Derived Nitrone with Allyl Alcohol: Synthesis of 2-Hydroxy-1-deoxycastanospermine Analogues</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The synthesis and evaluation of glycosidase inhibitory activity of polyhydroxylated indolizidine alkaloids namely 2-hydroxy-1-deoxycastanospermine 3a,b and 2-hydroxy-1-deoxy-8a-epi-castanospermine 3c,d is reported. The key step involves the intermolecular 1,3-dipolar cycloaddition of allyl alcohol to d-glucose-derived nitrone 4, followed by tosylation, that afforded four diastereomeric sugar-substituted isoxazolidines 5a−d with the desired regioselectivity. The one-pot conversion of 5a−d to pyrrolidines 8a−d by hydrogenolysis, removal of 1,2-acetonoide functionality, and hydrogenation afforded corresponding target molecules 3a−d.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Glucose - chemistry</subject><subject>Glycoside Hydrolases - antagonists & inhibitors</subject><subject>Glycoside Hydrolases - metabolism</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Indolizines</subject><subject>Inhibitory Concentration 50</subject><subject>Molecular Conformation</subject><subject>Molecular Structure</subject><subject>Nitrogen Oxides - chemistry</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Propanols - chemistry</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>eNptkM1OGzEUha2KqgTaRV8AzYYFEi6-49gzwy4Kf5VCSwldjxz_EIMzjuwJZHZs2fQh-yR1SEQ2vZbuseTvHl0fhL4C-QYkh5MHT_olFHz5AfWA5QTzivR3UI-QPMc053QX7cX4QFIxxj6hXWAF6VcF6aE_cEzxmZ17J0I27KTzQinbWt9kt1rIt4s3mcKXbiF91PhMB_ukVfbDtsE3Onu27TQbONe51KWfenf69-U1G3dNO9XRxtV0jq86Ffyyw4CVTipFbEXj41yHmU0mg0Y4f7_Q8TP6aISL-stG99Hvi_O74RUe_bz8PhyMsKAltLhM_5VCgCoNUYxWGpg0MDGmSkdNZAHAeDUpE0JNldMKOBCWl1pSA8ZIuo-O1r4y-BiDNvU82JkIXQ2kXmVav2ea2IM1O19MZlptyU2ICTjcACJK4UwQjbRxy3FGS8Z54vCas7HVy_d3ER5rXtCC1Xc34_oXuRmOr2_79fXWV8iY9lmElFL8z4L_ABdsnPE</recordid><startdate>20050218</startdate><enddate>20050218</enddate><creator>Karanjule, Narayan S</creator><creator>Markad, Shankar D</creator><creator>Sharma, Tarun</creator><creator>Sabharwal, Sushma G</creator><creator>Puranik, Vedavati G</creator><creator>Dhavale, Dilip D</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>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20050218</creationdate><title>1,3-Dipolar Cycloaddition Reaction of d-Glucose-Derived Nitrone with Allyl Alcohol: Synthesis of 2-Hydroxy-1-deoxycastanospermine Analogues</title><author>Karanjule, Narayan S ; Markad, Shankar D ; Sharma, Tarun ; Sabharwal, Sushma G ; Puranik, Vedavati G ; Dhavale, Dilip D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-8048caa1d8f0d539e15cf1bff9f9fdbc711569b8aa13f92391610528ec3f1ffc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Glucose - chemistry</topic><topic>Glycoside Hydrolases - antagonists & inhibitors</topic><topic>Glycoside Hydrolases - metabolism</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Indolizines</topic><topic>Inhibitory Concentration 50</topic><topic>Molecular Conformation</topic><topic>Molecular Structure</topic><topic>Nitrogen Oxides - chemistry</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Propanols - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Karanjule, Narayan S</creatorcontrib><creatorcontrib>Markad, Shankar D</creatorcontrib><creatorcontrib>Sharma, Tarun</creatorcontrib><creatorcontrib>Sabharwal, Sushma G</creatorcontrib><creatorcontrib>Puranik, Vedavati G</creatorcontrib><creatorcontrib>Dhavale, Dilip D</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>CrossRef</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Karanjule, Narayan S</au><au>Markad, Shankar D</au><au>Sharma, Tarun</au><au>Sabharwal, Sushma G</au><au>Puranik, Vedavati G</au><au>Dhavale, Dilip D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>1,3-Dipolar Cycloaddition Reaction of d-Glucose-Derived Nitrone with Allyl Alcohol: Synthesis of 2-Hydroxy-1-deoxycastanospermine Analogues</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2005-02-18</date><risdate>2005</risdate><volume>70</volume><issue>4</issue><spage>1356</spage><epage>1363</epage><pages>1356-1363</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The synthesis and evaluation of glycosidase inhibitory activity of polyhydroxylated indolizidine alkaloids namely 2-hydroxy-1-deoxycastanospermine 3a,b and 2-hydroxy-1-deoxy-8a-epi-castanospermine 3c,d is reported. The key step involves the intermolecular 1,3-dipolar cycloaddition of allyl alcohol to d-glucose-derived nitrone 4, followed by tosylation, that afforded four diastereomeric sugar-substituted isoxazolidines 5a−d with the desired regioselectivity. The one-pot conversion of 5a−d to pyrrolidines 8a−d by hydrogenolysis, removal of 1,2-acetonoide functionality, and hydrogenation afforded corresponding target molecules 3a−d.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15704970</pmid><doi>10.1021/jo048176x</doi><tpages>8</tpages></addata></record>
fulltext	fulltext
identifier	ISSN: 0022-3263
ispartof	Journal of organic chemistry, 2005-02, Vol.70 (4), p.1356-1363
issn	0022-3263 1520-6904
language	eng
recordid	cdi_crossref_primary_10_1021_jo048176x
source	American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects	Chemistry Exact sciences and technology Glucose - chemistry Glycoside Hydrolases - antagonists & inhibitors Glycoside Hydrolases - metabolism Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Indolizines Inhibitory Concentration 50 Molecular Conformation Molecular Structure Nitrogen Oxides - chemistry Organic chemistry Preparations and properties Propanols - chemistry Stereoisomerism
title	1,3-Dipolar Cycloaddition Reaction of d-Glucose-Derived Nitrone with Allyl Alcohol: Synthesis of 2-Hydroxy-1-deoxycastanospermine Analogues
url	http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T01%3A19%3A53IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=1,3-Dipolar%20Cycloaddition%20Reaction%20of%20d-Glucose-Derived%20Nitrone%20with%20Allyl%20Alcohol:%E2%80%89%20Synthesis%20of%202-Hydroxy-1-deoxycastanospermine%20Analogues&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Karanjule,%20Narayan%20S&rft.date=2005-02-18&rft.volume=70&rft.issue=4&rft.spage=1356&rft.epage=1363&rft.pages=1356-1363&rft.issn=0022-3263&rft.eissn=1520-6904&rft.coden=JOCEAH&rft_id=info:doi/10.1021/jo048176x&rft_dat=%3Cacs_cross%3Ec589241209%3C/acs_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a381t-8048caa1d8f0d539e15cf1bff9f9fdbc711569b8aa13f92391610528ec3f1ffc3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/15704970&rfr_iscdi=true