New Route to Branched-chain Aminodeoxy Sugars by Reaction of Ketoses with Acetonitrile. Synthesis of Methyl 3-C-2′-Aminoethyl-2-deoxy-α-D-arabino-hexopyranoside
Addition of methyl 4,6-O-benzylidene-2-deoxy-α- D -erythro-hexopyranosid-3-ulose ( 1 ) to acetonitrile in liquid ammonia at −50 to −60° in the presence of lithium amide gave, in high yield, crystalline methyl 4,6-O-benzylidene-3-C-cyanomethyl-2-deoxy-α- D -arabino-hexopyranoside ( 2 ) exclusively. T...
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| Veröffentlicht in: | Canadian journal of chemistry 1974-01, Vol.52 (1), p.51-54 |
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| container_title | Canadian journal of chemistry |
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| creator | Rosenthal, Alex Schöllnhammer, G |
| description | Addition of methyl 4,6-O-benzylidene-2-deoxy-α-
D
-erythro-hexopyranosid-3-ulose (
1
) to acetonitrile in liquid ammonia at −50 to −60° in the presence of lithium amide gave, in high yield, crystalline methyl 4,6-O-benzylidene-3-C-cyanomethyl-2-deoxy-α-
D
-arabino-hexopyranoside (
2
) exclusively. The proof of structure
2
is described. Debenzylidenation of
2
afforded the branched-chain cyano glycoside
3
. Compound
3
was converted into its 3,4,6-tri-O-acetate (
8
) and 4,6-di-O-p-nitrobenzoate (
9
) derivatives. Catalytic hydrogenation of
3
over rhodium on alumina yielded methyl 3-C-2′-aminoethyl-2-deoxy-α-
D
-arabino-hexopyranoside which was characterized as its N-2,4-dinitrophenyl derivative (
7
). |
| doi_str_mv | 10.1139/v74-008 |
| format | Article |
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D
-erythro-hexopyranosid-3-ulose (
1
) to acetonitrile in liquid ammonia at −50 to −60° in the presence of lithium amide gave, in high yield, crystalline methyl 4,6-O-benzylidene-3-C-cyanomethyl-2-deoxy-α-
D
-arabino-hexopyranoside (
2
) exclusively. The proof of structure
2
is described. Debenzylidenation of
2
afforded the branched-chain cyano glycoside
3
. Compound
3
was converted into its 3,4,6-tri-O-acetate (
8
) and 4,6-di-O-p-nitrobenzoate (
9
) derivatives. Catalytic hydrogenation of
3
over rhodium on alumina yielded methyl 3-C-2′-aminoethyl-2-deoxy-α-
D
-arabino-hexopyranoside which was characterized as its N-2,4-dinitrophenyl derivative (
7
).</description><identifier>ISSN: 0008-4042</identifier><identifier>EISSN: 1480-3291</identifier><identifier>DOI: 10.1139/v74-008</identifier><language>eng</language><publisher>Ottawa, Canada: NRC Research Press</publisher><ispartof>Canadian journal of chemistry, 1974-01, Vol.52 (1), p.51-54</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c254t-92e983502d2da4a17a314bc1f64f9f617d84cf0e91eb9b6be17bf7a8f648be2b3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://cdnsciencepub.com/doi/pdf/10.1139/v74-008$$EPDF$$P50$$Gnrcresearch$$H</linktopdf><linktohtml>$$Uhttps://cdnsciencepub.com/doi/full/10.1139/v74-008$$EHTML$$P50$$Gnrcresearch$$H</linktohtml><link.rule.ids>314,780,784,2932,27924,27925,64428,65234</link.rule.ids></links><search><creatorcontrib>Rosenthal, Alex</creatorcontrib><creatorcontrib>Schöllnhammer, G</creatorcontrib><title>New Route to Branched-chain Aminodeoxy Sugars by Reaction of Ketoses with Acetonitrile. Synthesis of Methyl 3-C-2′-Aminoethyl-2-deoxy-α-D-arabino-hexopyranoside</title><title>Canadian journal of chemistry</title><addtitle>Revue canadienne de chimie</addtitle><description>Addition of methyl 4,6-O-benzylidene-2-deoxy-α-
D
-erythro-hexopyranosid-3-ulose (
1
) to acetonitrile in liquid ammonia at −50 to −60° in the presence of lithium amide gave, in high yield, crystalline methyl 4,6-O-benzylidene-3-C-cyanomethyl-2-deoxy-α-
D
-arabino-hexopyranoside (
2
) exclusively. The proof of structure
2
is described. Debenzylidenation of
2
afforded the branched-chain cyano glycoside
3
. Compound
3
was converted into its 3,4,6-tri-O-acetate (
8
) and 4,6-di-O-p-nitrobenzoate (
9
) derivatives. Catalytic hydrogenation of
3
over rhodium on alumina yielded methyl 3-C-2′-aminoethyl-2-deoxy-α-
D
-arabino-hexopyranoside which was characterized as its N-2,4-dinitrophenyl derivative (
7
).</description><issn>0008-4042</issn><issn>1480-3291</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1974</creationdate><recordtype>article</recordtype><recordid>eNp9kE1OwzAQhS0EEuVHXMErkJAMtuM2ybKUX1FA4mcd2c6YGJW4sl0gO-7CCeAgHIKT4Ba2sBq9eZ_ejB5CW4zuMZaV-0-5IJQWS6jHREFJxku2jHo0rYiggq-itRAekswp7_fQ2yU842s3i4CjwwdetrqBmuhG2hYPH23ranAvHb6Z3UsfsOrwNUgdrWuxM_gcogsQ8LONDR7qpFobvZ3AHr7p2thAsGHOXUBsugnOyIjwr9cPsghe7AgniwPk850cEumlSg5p4MVNu_SMC7aGDbRi5CTA5u9cR3fHR7ejUzK-OjkbDcdE876IpORQFlmf8prXUkiWy4wJpZkZCFOaAcvrQmhDoWSgSjVQwHJlclkkv1DAVbaOdn5ytXcheDDV1NtH6buK0WrebZW6rVKRidz9IVuvPQSQXjf_wNt_w79QNa1N9g39-owj</recordid><startdate>19740101</startdate><enddate>19740101</enddate><creator>Rosenthal, Alex</creator><creator>Schöllnhammer, G</creator><general>NRC Research Press</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19740101</creationdate><title>New Route to Branched-chain Aminodeoxy Sugars by Reaction of Ketoses with Acetonitrile. Synthesis of Methyl 3-C-2′-Aminoethyl-2-deoxy-α-D-arabino-hexopyranoside</title><author>Rosenthal, Alex ; Schöllnhammer, G</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c254t-92e983502d2da4a17a314bc1f64f9f617d84cf0e91eb9b6be17bf7a8f648be2b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1974</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rosenthal, Alex</creatorcontrib><creatorcontrib>Schöllnhammer, G</creatorcontrib><collection>CrossRef</collection><jtitle>Canadian journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rosenthal, Alex</au><au>Schöllnhammer, G</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Route to Branched-chain Aminodeoxy Sugars by Reaction of Ketoses with Acetonitrile. Synthesis of Methyl 3-C-2′-Aminoethyl-2-deoxy-α-D-arabino-hexopyranoside</atitle><jtitle>Canadian journal of chemistry</jtitle><addtitle>Revue canadienne de chimie</addtitle><date>1974-01-01</date><risdate>1974</risdate><volume>52</volume><issue>1</issue><spage>51</spage><epage>54</epage><pages>51-54</pages><issn>0008-4042</issn><eissn>1480-3291</eissn><abstract>Addition of methyl 4,6-O-benzylidene-2-deoxy-α-
D
-erythro-hexopyranosid-3-ulose (
1
) to acetonitrile in liquid ammonia at −50 to −60° in the presence of lithium amide gave, in high yield, crystalline methyl 4,6-O-benzylidene-3-C-cyanomethyl-2-deoxy-α-
D
-arabino-hexopyranoside (
2
) exclusively. The proof of structure
2
is described. Debenzylidenation of
2
afforded the branched-chain cyano glycoside
3
. Compound
3
was converted into its 3,4,6-tri-O-acetate (
8
) and 4,6-di-O-p-nitrobenzoate (
9
) derivatives. Catalytic hydrogenation of
3
over rhodium on alumina yielded methyl 3-C-2′-aminoethyl-2-deoxy-α-
D
-arabino-hexopyranoside which was characterized as its N-2,4-dinitrophenyl derivative (
7
).</abstract><cop>Ottawa, Canada</cop><pub>NRC Research Press</pub><doi>10.1139/v74-008</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0008-4042 |
| ispartof | Canadian journal of chemistry, 1974-01, Vol.52 (1), p.51-54 |
| issn | 0008-4042 1480-3291 |
| language | eng |
| recordid | cdi_crossref_primary_10_1139_v74_008 |
| source | NRC Research Press; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| title | New Route to Branched-chain Aminodeoxy Sugars by Reaction of Ketoses with Acetonitrile. Synthesis of Methyl 3-C-2′-Aminoethyl-2-deoxy-α-D-arabino-hexopyranoside |
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