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A simple synthesis of 8-(methoxycarbonyl)octyl 3,6-di- O-(α- d-mannopyranosyl)-α- d-mannopyranoside and derivatives and their use in the preparation of neoglycoconjugates
8-(Methoxycarbonyl)octyl 3,6-di- O-(α- d-mannopyranosyl)-α- d-mannopyranoside ( 10) was synthesized in 54% yield by regioselective diglycosylation of unprotected mannoside 4, employing the trichloroacetimidate donor 1, followed by debenzoylation. Derivatives of compounds 4 and 10 were used to prepar...
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| Published in: | Carbohydrate research 1999-01, Vol.315 (1), p.148-158 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c385t-b88c5ea4dccaf68de2840f060e810b1b487949e8df3e7221fb8c0bc531b3b2063 |
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| cites | cdi_FETCH-LOGICAL-c385t-b88c5ea4dccaf68de2840f060e810b1b487949e8df3e7221fb8c0bc531b3b2063 |
| container_end_page | 158 |
| container_issue | 1 |
| container_start_page | 148 |
| container_title | Carbohydrate research |
| container_volume | 315 |
| creator | Becker, Bernd Furneaux, Richard H Reck, Folkert Zubkov, Oleg A |
| description | 8-(Methoxycarbonyl)octyl 3,6-di-
O-(α-
d-mannopyranosyl)-α-
d-mannopyranoside (
10) was synthesized in 54% yield by regioselective diglycosylation of unprotected mannoside
4, employing the trichloroacetimidate donor
1, followed by debenzoylation. Derivatives of compounds
4 and
10 were used to prepare conjugates containing fluorochromes for the study of carbohydrate–lectin interactions, as well as conjugates with phospholipids for the preparation of liposomes. |
| doi_str_mv | 10.1016/S0008-6215(98)00330-9 |
| format | article |
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d-mannopyranosyl)-α-
d-mannopyranoside (
10) was synthesized in 54% yield by regioselective diglycosylation of unprotected mannoside
4, employing the trichloroacetimidate donor
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4 and
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O-(α-
d-mannopyranosyl)-α-
d-mannopyranoside (
10) was synthesized in 54% yield by regioselective diglycosylation of unprotected mannoside
4, employing the trichloroacetimidate donor
1, followed by debenzoylation. Derivatives of compounds
4 and
10 were used to prepare conjugates containing fluorochromes for the study of carbohydrate–lectin interactions, as well as conjugates with phospholipids for the preparation of liposomes.</description><subject>Carbohydrate Sequence</subject><subject>Disaccharides - chemical synthesis</subject><subject>Glycoconjugates - chemical synthesis</subject><subject>Glycolipid</subject><subject>glycolipids</subject><subject>Mannosides - chemical synthesis</subject><subject>Mannotrioside</subject><subject>Molecular Sequence Data</subject><subject>Neoglycoconjugates</subject><subject>oligosaccharides</subject><subject>Synthesis</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><recordid>eNqFkc2KFDEUhYMoTjv6CGpW0gNGb-o3tZJh8A8GZjEOuAup5FZPhqqkTKoa653c-CI-k-muQQQXrsIJ3805N4eQ5xzecODV22sAEKzKeLltxBlAngNrHpANF3XOiqz6-pBs_iAn5EmMd0lCVVePyQmHXJRNLTbkxzmNdhh7pHFx0y1GG6nvqGDbAadb_33RKrTeLf2Z19PS0_x1xYxl9Iptf_1k1LBBOefHJSjnY6LYv7fWIFXOUIPB7tVk9xiPOrnZQOeI1LqDoGPAUYVEeHfI4NDv-kV77d3dvFMTxqfkUaf6iM_uz1Ny8-H9l4tP7PLq4-eL80um01oTa4XQJarCaK26ShjMRAEdVICCQ8vbQtRN0aAwXY51lvGuFRpaXea8zdsMqvyUvFrfHYP_NmOc5GCjxr5XKdMcZdWIMiuhTGC5gjr4GAN2cgx2UGGRHOShJnmsSR46kI2Qx5pkk-Ze3BvM7YDmr6m1lwS8XIFOeal2wUZ5c50BzyFroEjeiXi3Epg-Ym8xyKgtOo3GBtSTNN7-J8RvNj6vhA</recordid><startdate>19990131</startdate><enddate>19990131</enddate><creator>Becker, Bernd</creator><creator>Furneaux, Richard H</creator><creator>Reck, Folkert</creator><creator>Zubkov, Oleg A</creator><general>Elsevier Ltd</general><scope>FBQ</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>19990131</creationdate><title>A simple synthesis of 8-(methoxycarbonyl)octyl 3,6-di- O-(α- d-mannopyranosyl)-α- d-mannopyranoside and derivatives and their use in the preparation of neoglycoconjugates</title><author>Becker, Bernd ; Furneaux, Richard H ; Reck, Folkert ; Zubkov, Oleg A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c385t-b88c5ea4dccaf68de2840f060e810b1b487949e8df3e7221fb8c0bc531b3b2063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Carbohydrate Sequence</topic><topic>Disaccharides - chemical synthesis</topic><topic>Glycoconjugates - chemical synthesis</topic><topic>Glycolipid</topic><topic>glycolipids</topic><topic>Mannosides - chemical synthesis</topic><topic>Mannotrioside</topic><topic>Molecular Sequence Data</topic><topic>Neoglycoconjugates</topic><topic>oligosaccharides</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Becker, Bernd</creatorcontrib><creatorcontrib>Furneaux, Richard H</creatorcontrib><creatorcontrib>Reck, Folkert</creatorcontrib><creatorcontrib>Zubkov, Oleg A</creatorcontrib><collection>AGRIS</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>Becker, Bernd</au><au>Furneaux, Richard H</au><au>Reck, Folkert</au><au>Zubkov, Oleg A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A simple synthesis of 8-(methoxycarbonyl)octyl 3,6-di- O-(α- d-mannopyranosyl)-α- d-mannopyranoside and derivatives and their use in the preparation of neoglycoconjugates</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>1999-01-31</date><risdate>1999</risdate><volume>315</volume><issue>1</issue><spage>148</spage><epage>158</epage><pages>148-158</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><abstract>8-(Methoxycarbonyl)octyl 3,6-di-
O-(α-
d-mannopyranosyl)-α-
d-mannopyranoside (
10) was synthesized in 54% yield by regioselective diglycosylation of unprotected mannoside
4, employing the trichloroacetimidate donor
1, followed by debenzoylation. Derivatives of compounds
4 and
10 were used to prepare conjugates containing fluorochromes for the study of carbohydrate–lectin interactions, as well as conjugates with phospholipids for the preparation of liposomes.</abstract><cop>Netherlands</cop><pub>Elsevier Ltd</pub><pmid>10385978</pmid><doi>10.1016/S0008-6215(98)00330-9</doi><tpages>11</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-6215 |
| ispartof | Carbohydrate research, 1999-01, Vol.315 (1), p.148-158 |
| issn | 0008-6215 1873-426X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_69852505 |
| source | Elsevier |
| subjects | Carbohydrate Sequence Disaccharides - chemical synthesis Glycoconjugates - chemical synthesis Glycolipid glycolipids Mannosides - chemical synthesis Mannotrioside Molecular Sequence Data Neoglycoconjugates oligosaccharides Synthesis |
| title | A simple synthesis of 8-(methoxycarbonyl)octyl 3,6-di- O-(α- d-mannopyranosyl)-α- d-mannopyranoside and derivatives and their use in the preparation of neoglycoconjugates |
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