3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethylidene]-[beta]-d-mannopyranose 0.11-hydrate

The title compound, C16H24O10·0.11H2O, is a key intermediate in the synthesis of 2-deoxy-2-[18F]fluoro-d-glucose (18F-FDG), which is the most widely used molecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent molecules (A and B) in the asymmetric un...

Full description

Saved in:
Bibliographic Details
Published in:Acta crystallographica. Section C, Crystal structure communications Crystal structure communications, 2012-09, Vol.68 (9), p.o338
Main Authors: Liu, Ya-Ling, Zou, Pei, Wu, Hao, Xie, Min-Hao, Luo, Shi-Neng
Format: Article
Language:English
Subjects:
Chemical synthesis
Crystal structure
Crystallography
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites
container_end_page
container_issue 9
container_start_page o338
container_title Acta crystallographica. Section C, Crystal structure communications
container_volume 68
creator Liu, Ya-Ling
Zou, Pei
Wu, Hao
Xie, Min-Hao
Luo, Shi-Neng
description The title compound, C16H24O10·0.11H2O, is a key intermediate in the synthesis of 2-deoxy-2-[18F]fluoro-d-glucose (18F-FDG), which is the most widely used molecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent molecules (A and B) in the asymmetric unit, with closely comparable geometries. The pyranose ring adopts a 4C1 conformation [Cremer-Pople puckering parameters: Q = 0.553(2)Å, [theta] = 16.2(2)° and = 290.4(8)° for molecule A, and Q = 0.529(2)Å, [theta] =15.3(3)° and = 268.2(9)° for molecule B], and the dioxolane ring adopts an envelope conformation. The chiral centre in the dioxolane ring, introduced during the synthesis of the compound, has an R configuration, with the ethoxy group exo to the mannopyranose ring. The asymmetric unit also contains one water molecule with a refined site-occupancy factor of 0.222(8), which bridges between molecules A and B via O--H...O hydrogen bonds. [PUBLICATION ABSTRACT]
doi_str_mv 10.1107/S0108270112032076
format article
fullrecord <record><control><sourceid>proquest</sourceid><recordid>TN_cdi_proquest_journals_1037608321</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2750342121</sourcerecordid><originalsourceid>FETCH-proquest_journals_10376083213</originalsourceid><addsrcrecordid>eNqNjsFqAjEURUOx0LH1A7oT3CjMa99LdKJrUdy5qNCFiKTOKypjokkE8_fOgB_g6nA5Z3GF-CT8IkL9_YOEY6mRSKKSqIsXkVGBCCM9mrRE1mho_Jtoh3BERCmlysSvyod5ASt_gCWYHcdUAeWyHmuCPt8ccNy7WxrUSNWhZMsbWP9xNBso4WSsdefkjXWBu80V2KfSm8gf4vXfVIE7D76L3ny2mi7g7N3lyiFuj-7qba22hEoXOFaS1HPVHRA-RLY</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1037608321</pqid></control><display><type>article</type><title>3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethylidene]-[beta]-d-mannopyranose 0.11-hydrate</title><source>Wiley-Blackwell Read &amp; Publish Collection</source><source>Alma/SFX Local Collection</source><creator>Liu, Ya-Ling ; Zou, Pei ; Wu, Hao ; Xie, Min-Hao ; Luo, Shi-Neng</creator><creatorcontrib>Liu, Ya-Ling ; Zou, Pei ; Wu, Hao ; Xie, Min-Hao ; Luo, Shi-Neng</creatorcontrib><description>The title compound, C16H24O10·0.11H2O, is a key intermediate in the synthesis of 2-deoxy-2-[18F]fluoro-d-glucose (18F-FDG), which is the most widely used molecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent molecules (A and B) in the asymmetric unit, with closely comparable geometries. The pyranose ring adopts a 4C1 conformation [Cremer-Pople puckering parameters: Q = 0.553(2)Å, [theta] = 16.2(2)° and = 290.4(8)° for molecule A, and Q = 0.529(2)Å, [theta] =15.3(3)° and = 268.2(9)° for molecule B], and the dioxolane ring adopts an envelope conformation. The chiral centre in the dioxolane ring, introduced during the synthesis of the compound, has an R configuration, with the ethoxy group exo to the mannopyranose ring. The asymmetric unit also contains one water molecule with a refined site-occupancy factor of 0.222(8), which bridges between molecules A and B via O--H...O hydrogen bonds. [PUBLICATION ABSTRACT]</description><identifier>ISSN: 0108-2701</identifier><identifier>EISSN: 1600-5759</identifier><identifier>DOI: 10.1107/S0108270112032076</identifier><language>eng</language><publisher>Chester: Wiley Subscription Services, Inc</publisher><subject>Chemical synthesis ; Crystal structure ; Crystallography</subject><ispartof>Acta crystallographica. Section C, Crystal structure communications, 2012-09, Vol.68 (9), p.o338</ispartof><rights>International Union of Crystallography, 2012</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>Liu, Ya-Ling</creatorcontrib><creatorcontrib>Zou, Pei</creatorcontrib><creatorcontrib>Wu, Hao</creatorcontrib><creatorcontrib>Xie, Min-Hao</creatorcontrib><creatorcontrib>Luo, Shi-Neng</creatorcontrib><title>3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethylidene]-[beta]-d-mannopyranose 0.11-hydrate</title><title>Acta crystallographica. Section C, Crystal structure communications</title><description>The title compound, C16H24O10·0.11H2O, is a key intermediate in the synthesis of 2-deoxy-2-[18F]fluoro-d-glucose (18F-FDG), which is the most widely used molecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent molecules (A and B) in the asymmetric unit, with closely comparable geometries. The pyranose ring adopts a 4C1 conformation [Cremer-Pople puckering parameters: Q = 0.553(2)Å, [theta] = 16.2(2)° and = 290.4(8)° for molecule A, and Q = 0.529(2)Å, [theta] =15.3(3)° and = 268.2(9)° for molecule B], and the dioxolane ring adopts an envelope conformation. The chiral centre in the dioxolane ring, introduced during the synthesis of the compound, has an R configuration, with the ethoxy group exo to the mannopyranose ring. The asymmetric unit also contains one water molecule with a refined site-occupancy factor of 0.222(8), which bridges between molecules A and B via O--H...O hydrogen bonds. [PUBLICATION ABSTRACT]</description><subject>Chemical synthesis</subject><subject>Crystal structure</subject><subject>Crystallography</subject><issn>0108-2701</issn><issn>1600-5759</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqNjsFqAjEURUOx0LH1A7oT3CjMa99LdKJrUdy5qNCFiKTOKypjokkE8_fOgB_g6nA5Z3GF-CT8IkL9_YOEY6mRSKKSqIsXkVGBCCM9mrRE1mho_Jtoh3BERCmlysSvyod5ASt_gCWYHcdUAeWyHmuCPt8ccNy7WxrUSNWhZMsbWP9xNBso4WSsdefkjXWBu80V2KfSm8gf4vXfVIE7D76L3ny2mi7g7N3lyiFuj-7qba22hEoXOFaS1HPVHRA-RLY</recordid><startdate>20120901</startdate><enddate>20120901</enddate><creator>Liu, Ya-Ling</creator><creator>Zou, Pei</creator><creator>Wu, Hao</creator><creator>Xie, Min-Hao</creator><creator>Luo, Shi-Neng</creator><general>Wiley Subscription Services, Inc</general><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20120901</creationdate><title>3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethylidene]-[beta]-d-mannopyranose 0.11-hydrate</title><author>Liu, Ya-Ling ; Zou, Pei ; Wu, Hao ; Xie, Min-Hao ; Luo, Shi-Neng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-proquest_journals_10376083213</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Chemical synthesis</topic><topic>Crystal structure</topic><topic>Crystallography</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Ya-Ling</creatorcontrib><creatorcontrib>Zou, Pei</creatorcontrib><creatorcontrib>Wu, Hao</creatorcontrib><creatorcontrib>Xie, Min-Hao</creatorcontrib><creatorcontrib>Luo, Shi-Neng</creatorcontrib><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Ya-Ling</au><au>Zou, Pei</au><au>Wu, Hao</au><au>Xie, Min-Hao</au><au>Luo, Shi-Neng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethylidene]-[beta]-d-mannopyranose 0.11-hydrate</atitle><jtitle>Acta crystallographica. Section C, Crystal structure communications</jtitle><date>2012-09-01</date><risdate>2012</risdate><volume>68</volume><issue>9</issue><spage>o338</spage><pages>o338-</pages><issn>0108-2701</issn><eissn>1600-5759</eissn><abstract>The title compound, C16H24O10·0.11H2O, is a key intermediate in the synthesis of 2-deoxy-2-[18F]fluoro-d-glucose (18F-FDG), which is the most widely used molecular-imaging probe for positron emission tomography (PET). The crystal structure has two independent molecules (A and B) in the asymmetric unit, with closely comparable geometries. The pyranose ring adopts a 4C1 conformation [Cremer-Pople puckering parameters: Q = 0.553(2)Å, [theta] = 16.2(2)° and = 290.4(8)° for molecule A, and Q = 0.529(2)Å, [theta] =15.3(3)° and = 268.2(9)° for molecule B], and the dioxolane ring adopts an envelope conformation. The chiral centre in the dioxolane ring, introduced during the synthesis of the compound, has an R configuration, with the ethoxy group exo to the mannopyranose ring. The asymmetric unit also contains one water molecule with a refined site-occupancy factor of 0.222(8), which bridges between molecules A and B via O--H...O hydrogen bonds. [PUBLICATION ABSTRACT]</abstract><cop>Chester</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1107/S0108270112032076</doi></addata></record>
fulltext fulltext
identifier ISSN: 0108-2701
ispartof Acta crystallographica. Section C, Crystal structure communications, 2012-09, Vol.68 (9), p.o338
issn 0108-2701
1600-5759
language eng
recordid cdi_proquest_journals_1037608321
source Wiley-Blackwell Read & Publish Collection; Alma/SFX Local Collection
subjects Chemical synthesis
Crystal structure
Crystallography
title 3,4,6-Tri-O-acetyl-1,2-O-[1-(exo-ethoxy)ethylidene]-[beta]-d-mannopyranose 0.11-hydrate
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-17T19%3A48%3A06IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=3,4,6-Tri-O-acetyl-1,2-O-%5B1-(exo-ethoxy)ethylidene%5D-%5Bbeta%5D-d-mannopyranose%200.11-hydrate&rft.jtitle=Acta%20crystallographica.%20Section%20C,%20Crystal%20structure%20communications&rft.au=Liu,%20Ya-Ling&rft.date=2012-09-01&rft.volume=68&rft.issue=9&rft.spage=o338&rft.pages=o338-&rft.issn=0108-2701&rft.eissn=1600-5759&rft_id=info:doi/10.1107/S0108270112032076&rft_dat=%3Cproquest%3E2750342121%3C/proquest%3E%3Cgrp_id%3Ecdi_FETCH-proquest_journals_10376083213%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1037608321&rft_id=info:pmid/&rfr_iscdi=true