Synthesis of a selectively protected trisaccharide building block that is part of xylose-containing carbohydrate chains from N-glycoproteins
The synthesis is reported of ethyl 4- O-[3- O-allyl-4,6- O-isopropylidene-2- O-(2,3,4-tri- O-acetyl-β- d- xylopyranosyl)-β- d-mannopyranosyl]-3,6-di- O-benzyl-2-deoxy-2-phthalimido-1-thio-β- d-glucopyranoside ( 16), a key intermediate in the synthesis of xylose-containing carbohydrate chains from N-...
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| Veröffentlicht in: | Carbohydrate research 1993-01, Vol.238, p.135-145 |
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| creator | Kerékgyártó, János van der Ven, Jos G.M. Kamerling, Johannis P. Lipták, András Vliegenthart, Johannes F.G. |
| description | The synthesis is reported of ethyl 4-
O-[3-
O-allyl-4,6-
O-isopropylidene-2-
O-(2,3,4-tri-
O-acetyl-β-
d- xylopyranosyl)-β-
d-mannopyranosyl]-3,6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
16), a key intermediate in the synthesis of xylose-containing carbohydrate chains from N-glycoproteins. Condensation of ethyl 3,6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
5) with 2,4,6-tri-
O-acetyl-3-
O-allyl-α-
d-glucopyranosyl bromide, using silver triflate as a promoter, gave the β-linked disaccharide derivative
8 (84%).
O-Deacetylation of
8 and then isopropylidenation afforded
10, which was converted via oxidation-reduction into ethyl 4-
O-allyl-4,6-
O-isopropylidene-β-
d-mannopyranosyl)-3, 6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
12). Silver triflate-promoted condensation of
12 with 2,3,4-tri-
O-acetyl-α-
d-xylopyranosyl bromide gave
16 (71%). The Xyl
p unit in
16 and in de-isopropylidenated
16 (
17) existed in the
1
C
4(
d) conformation, but that in
O-deacetylated
17 (
18) existed in the
4
C
1(
d) conformation. |
| doi_str_mv | 10.1016/0008-6215(93)87009-H |
| format | Article |
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O-[3-
O-allyl-4,6-
O-isopropylidene-2-
O-(2,3,4-tri-
O-acetyl-β-
d- xylopyranosyl)-β-
d-mannopyranosyl]-3,6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
16), a key intermediate in the synthesis of xylose-containing carbohydrate chains from N-glycoproteins. Condensation of ethyl 3,6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
5) with 2,4,6-tri-
O-acetyl-3-
O-allyl-α-
d-glucopyranosyl bromide, using silver triflate as a promoter, gave the β-linked disaccharide derivative
8 (84%).
O-Deacetylation of
8 and then isopropylidenation afforded
10, which was converted via oxidation-reduction into ethyl 4-
O-allyl-4,6-
O-isopropylidene-β-
d-mannopyranosyl)-3, 6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
12). Silver triflate-promoted condensation of
12 with 2,3,4-tri-
O-acetyl-α-
d-xylopyranosyl bromide gave
16 (71%). The Xyl
p unit in
16 and in de-isopropylidenated
16 (
17) existed in the
1
C
4(
d) conformation, but that in
O-deacetylated
17 (
18) existed in the
4
C
1(
d) conformation.</description><identifier>ISSN: 0008-6215</identifier><identifier>EISSN: 1873-426X</identifier><identifier>DOI: 10.1016/0008-6215(93)87009-H</identifier><identifier>PMID: 8431931</identifier><identifier>CODEN: CRBRAT</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>Carbohydrate Conformation ; Carbohydrate Sequence ; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides ; Carbohydrates. Nucleosides and nucleotides ; Chemistry ; Exact sciences and technology ; Glycoproteins - chemical synthesis ; Glycoproteins - chemistry ; Glycosides - chemical synthesis ; Magnetic Resonance Spectroscopy ; Molecular Sequence Data ; Oligosaccharides - chemical synthesis ; Oligosaccharides - chemistry ; Organic chemistry ; Preparations and properties ; Trisaccharides - chemical synthesis ; Trisaccharides - chemistry</subject><ispartof>Carbohydrate research, 1993-01, Vol.238, p.135-145</ispartof><rights>1993</rights><rights>1993 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c463t-a688685e6030a082bf95524a81a970638e266ec24682a60eab658fd584129ff13</citedby><cites>FETCH-LOGICAL-c463t-a688685e6030a082bf95524a81a970638e266ec24682a60eab658fd584129ff13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/0008-6215(93)87009-H$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,45974</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=4541911$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8431931$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kerékgyártó, János</creatorcontrib><creatorcontrib>van der Ven, Jos G.M.</creatorcontrib><creatorcontrib>Kamerling, Johannis P.</creatorcontrib><creatorcontrib>Lipták, András</creatorcontrib><creatorcontrib>Vliegenthart, Johannes F.G.</creatorcontrib><title>Synthesis of a selectively protected trisaccharide building block that is part of xylose-containing carbohydrate chains from N-glycoproteins</title><title>Carbohydrate research</title><addtitle>Carbohydr Res</addtitle><description>The synthesis is reported of ethyl 4-
O-[3-
O-allyl-4,6-
O-isopropylidene-2-
O-(2,3,4-tri-
O-acetyl-β-
d- xylopyranosyl)-β-
d-mannopyranosyl]-3,6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
16), a key intermediate in the synthesis of xylose-containing carbohydrate chains from N-glycoproteins. Condensation of ethyl 3,6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
5) with 2,4,6-tri-
O-acetyl-3-
O-allyl-α-
d-glucopyranosyl bromide, using silver triflate as a promoter, gave the β-linked disaccharide derivative
8 (84%).
O-Deacetylation of
8 and then isopropylidenation afforded
10, which was converted via oxidation-reduction into ethyl 4-
O-allyl-4,6-
O-isopropylidene-β-
d-mannopyranosyl)-3, 6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
12). Silver triflate-promoted condensation of
12 with 2,3,4-tri-
O-acetyl-α-
d-xylopyranosyl bromide gave
16 (71%). The Xyl
p unit in
16 and in de-isopropylidenated
16 (
17) existed in the
1
C
4(
d) conformation, but that in
O-deacetylated
17 (
18) existed in the
4
C
1(
d) conformation.</description><subject>Carbohydrate Conformation</subject><subject>Carbohydrate Sequence</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>Glycoproteins - chemical synthesis</subject><subject>Glycoproteins - chemistry</subject><subject>Glycosides - chemical synthesis</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Molecular Sequence Data</subject><subject>Oligosaccharides - chemical synthesis</subject><subject>Oligosaccharides - chemistry</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Trisaccharides - chemical synthesis</subject><subject>Trisaccharides - chemistry</subject><issn>0008-6215</issn><issn>1873-426X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1993</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc-OFCEQh4nRrLOrb6AJB2PWQys0fxouJmajjslGD2rijdB09Q7KNLPAbOx38KGldyZz1BMp6qtfET6EnlHymhIq3xBCVCNbKi41e6U6QnSzfoBWVHWs4a388RCtTshjdJ7zz1oS2ckzdKY4o5rRFfrzdZ7KBrLPOI7Y4gwBXPF3EGa8S7HUAgZcks_WuY1NfgDc730Y_HSD-xDdL1w2tuA6v7OpLCG_5xAzNC5Oxfpp4ZxNfdzMQ7IFcE3xU8Zjilv8ubkJs4v3i-rlE_RotCHD0-N5gb5_eP_tat1cf_n46erddeO4ZKWxUimpBEjCiCWq7UctRMutolZ3RDIFrZTgWi5VayUB20uhxkEoTls9jpRdoJeH3Lr4dg-5mK3PDkKwE8R9Np0QkmnN_wtSKUgnSFtBfgBdijknGM0u-a1Ns6HELLbMosIsKoxm5t6WWdex58f8fb-F4TR01FP7L459m50NY7KT8_mEccGppgv29oBB_bQ7D8lk52FyMPhUBZoh-n-_4y8AwrLO</recordid><startdate>19930115</startdate><enddate>19930115</enddate><creator>Kerékgyártó, János</creator><creator>van der Ven, Jos G.M.</creator><creator>Kamerling, Johannis P.</creator><creator>Lipták, András</creator><creator>Vliegenthart, Johannes F.G.</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>19930115</creationdate><title>Synthesis of a selectively protected trisaccharide building block that is part of xylose-containing carbohydrate chains from N-glycoproteins</title><author>Kerékgyártó, János ; van der Ven, Jos G.M. ; Kamerling, Johannis P. ; Lipták, András ; Vliegenthart, Johannes F.G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c463t-a688685e6030a082bf95524a81a970638e266ec24682a60eab658fd584129ff13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1993</creationdate><topic>Carbohydrate Conformation</topic><topic>Carbohydrate Sequence</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>Glycoproteins - chemical synthesis</topic><topic>Glycoproteins - chemistry</topic><topic>Glycosides - chemical synthesis</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Molecular Sequence Data</topic><topic>Oligosaccharides - chemical synthesis</topic><topic>Oligosaccharides - chemistry</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Trisaccharides - chemical synthesis</topic><topic>Trisaccharides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kerékgyártó, János</creatorcontrib><creatorcontrib>van der Ven, Jos G.M.</creatorcontrib><creatorcontrib>Kamerling, Johannis P.</creatorcontrib><creatorcontrib>Lipták, András</creatorcontrib><creatorcontrib>Vliegenthart, Johannes F.G.</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>Kerékgyártó, János</au><au>van der Ven, Jos G.M.</au><au>Kamerling, Johannis P.</au><au>Lipták, András</au><au>Vliegenthart, Johannes F.G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of a selectively protected trisaccharide building block that is part of xylose-containing carbohydrate chains from N-glycoproteins</atitle><jtitle>Carbohydrate research</jtitle><addtitle>Carbohydr Res</addtitle><date>1993-01-15</date><risdate>1993</risdate><volume>238</volume><spage>135</spage><epage>145</epage><pages>135-145</pages><issn>0008-6215</issn><eissn>1873-426X</eissn><coden>CRBRAT</coden><abstract>The synthesis is reported of ethyl 4-
O-[3-
O-allyl-4,6-
O-isopropylidene-2-
O-(2,3,4-tri-
O-acetyl-β-
d- xylopyranosyl)-β-
d-mannopyranosyl]-3,6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
16), a key intermediate in the synthesis of xylose-containing carbohydrate chains from N-glycoproteins. Condensation of ethyl 3,6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
5) with 2,4,6-tri-
O-acetyl-3-
O-allyl-α-
d-glucopyranosyl bromide, using silver triflate as a promoter, gave the β-linked disaccharide derivative
8 (84%).
O-Deacetylation of
8 and then isopropylidenation afforded
10, which was converted via oxidation-reduction into ethyl 4-
O-allyl-4,6-
O-isopropylidene-β-
d-mannopyranosyl)-3, 6-di-
O-benzyl-2-deoxy-2-phthalimido-1-thio-β-
d-glucopyranoside (
12). Silver triflate-promoted condensation of
12 with 2,3,4-tri-
O-acetyl-α-
d-xylopyranosyl bromide gave
16 (71%). The Xyl
p unit in
16 and in de-isopropylidenated
16 (
17) existed in the
1
C
4(
d) conformation, but that in
O-deacetylated
17 (
18) existed in the
4
C
1(
d) conformation.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>8431931</pmid><doi>10.1016/0008-6215(93)87009-H</doi><tpages>11</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-6215 |
| ispartof | Carbohydrate research, 1993-01, Vol.238, p.135-145 |
| issn | 0008-6215 1873-426X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_75563994 |
| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Carbohydrate Conformation Carbohydrate Sequence Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Glycoproteins - chemical synthesis Glycoproteins - chemistry Glycosides - chemical synthesis Magnetic Resonance Spectroscopy Molecular Sequence Data Oligosaccharides - chemical synthesis Oligosaccharides - chemistry Organic chemistry Preparations and properties Trisaccharides - chemical synthesis Trisaccharides - chemistry |
| title | Synthesis of a selectively protected trisaccharide building block that is part of xylose-containing carbohydrate chains from N-glycoproteins |
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