General methods for modification of sialic acid at C-9. Synthesis of N-acetyl-9-deoxy-9-fluoroneuraminic acid

General methods for modification of sialic acid at C-9. Synthesis of N-acetyl-9-deoxy-9-fluoroneuraminic acid

Methyl 5-acetamido-3,5-dideoxy-2- O-methyl- d- glycero- d- galacto-2-nonulopyranosate was converted into the 9- O-trityl derivative and the remaining hydroxyl groups were protected as benzyl ethers. Removal of the trityl group, followed by treatment with diethylaminosulfur trifluoride gave the 9-deo...

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Veröffentlicht in:Carbohydrate research 1988-04, Vol.175 (1), p.25-34
Hauptverfasser: Sharma, Moheswar, Petrie, Charles R., Korytnyk, Walter
Format: Artikel
Sprache:eng
Schlagworte:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Indicators and Reagents
Magnetic Resonance Spectroscopy
Optical Rotation
Organic chemistry
Preparations and properties
Sialic Acids - chemical synthesis
Spectrophotometry, Infrared
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container_issue 1
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container_title Carbohydrate research
container_volume 175
creator Sharma, Moheswar
Petrie, Charles R.
Korytnyk, Walter
description Methyl 5-acetamido-3,5-dideoxy-2- O-methyl- d- glycero- d- galacto-2-nonulopyranosate was converted into the 9- O-trityl derivative and the remaining hydroxyl groups were protected as benzyl ethers. Removal of the trityl group, followed by treatment with diethylaminosulfur trifluoride gave the 9-deoxy-9-fluoro derivative, and deprotection N-acetyl-9-deoxy-9-fluoroneuraminic acid ( 8). In another procedure, coupling of 2-acetamido-2,6-dideoxy-6-fluoro- d-glucopyranose with potassium di( tert-butyl) oxaloacetate, followed by hydrolysis and decarboxylation gave 8. Some of the derivatives were active as inhibitors of growth of mouse mammary adenocarcinoma (TA 3) and L1210 cells in culture.
doi_str_mv 10.1016/0008-6215(88)80153-8
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Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Indicators and Reagents</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Optical Rotation</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Sialic Acids - chemical synthesis</subject><subject>Spectrophotometry, Infrared</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMFq3DAQhkVpSLdp3qAFHUppDkol2ZblS6AsSRoI6aEt9Cbk0Ygo2FYi2SH79rWzZo89DcN8_2j0EfJR8HPBhfrGOddMSVF91fpMc1EVTL8hG6HrgpVS_X1LNgfkHXmf88PcclWrY3JcFLWWJd-Q_hoHTLajPY730WXqY6J9dMEHsGOIA42e5mC7ANRCcNSOdMuac_prN4z3mENegDtmAcddxxrmML7s5uq7KaY44JRsH4Y1_YEcedtlPF3rCflzdfl7-4Pd_ry-2X6_ZVBoNTIQqBAU2kZyC3VpC1e1beml1K2r6lbWbaO4QATfiLLxLUgnUFu9dLqRxQn5st_7mOLThHk0fciAXWcHjFM28-crJYsFLPcgpJhzQm8eU-ht2hnBzWLZLArNotBobV4tGz3HPq37p7ZHdwitWuf553VuM9jOJztAyAesrpr5eTFjF3sMZxfPAZPJEHAAdCEhjMbF8P87_gGOcJig</recordid><startdate>19880401</startdate><enddate>19880401</enddate><creator>Sharma, Moheswar</creator><creator>Petrie, Charles R.</creator><creator>Korytnyk, Walter</creator><general>Elsevier Ltd</general><general>Elsevier Science</general><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><scope>7X8</scope></search><sort><creationdate>19880401</creationdate><title>General methods for modification of sialic acid at C-9. 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Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Indicators and Reagents</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Optical Rotation</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Sialic Acids - chemical synthesis</topic><topic>Spectrophotometry, Infrared</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sharma, Moheswar</creatorcontrib><creatorcontrib>Petrie, Charles R.</creatorcontrib><creatorcontrib>Korytnyk, Walter</creatorcontrib><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><collection>MEDLINE - Academic</collection><jtitle>Carbohydrate research</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sharma, Moheswar</au><au>Petrie, Charles R.</au><au>Korytnyk, Walter</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>General methods for modification of sialic acid at C-9. Synthesis of N-acetyl-9-deoxy-9-fluoroneuraminic acid</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>1988-04-01</date><risdate>1988</risdate><volume>175</volume><issue>1</issue><spage>25</spage><epage>34</epage><pages>25-34</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><coden>CRBRAT</coden><abstract>Methyl 5-acetamido-3,5-dideoxy-2- O-methyl- d- glycero- d- galacto-2-nonulopyranosate was converted into the 9- O-trityl derivative and the remaining hydroxyl groups were protected as benzyl ethers. Removal of the trityl group, followed by treatment with diethylaminosulfur trifluoride gave the 9-deoxy-9-fluoro derivative, and deprotection N-acetyl-9-deoxy-9-fluoroneuraminic acid ( 8). In another procedure, coupling of 2-acetamido-2,6-dideoxy-6-fluoro- d-glucopyranose with potassium di( tert-butyl) oxaloacetate, followed by hydrolysis and decarboxylation gave 8. 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subjects Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Exact sciences and technology
Indicators and Reagents
Magnetic Resonance Spectroscopy
Optical Rotation
Organic chemistry
Preparations and properties
Sialic Acids - chemical synthesis
Spectrophotometry, Infrared
title General methods for modification of sialic acid at C-9. Synthesis of N-acetyl-9-deoxy-9-fluoroneuraminic acid
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