An Unusual C-1C-2 Ring-Splitting of Pyranosides by a Retro-Aldol Reaction - a Route to New Chiral Building Blocks
The treatment of the α‐oxoketene dithioacetal sugar derivatives 2 and 7 with concentrated hydrochloric acid in THF leads to the open‐chain uloses 3 and 8. The reaction mechanism can be rationalized as a retro‐aldol reaction. This rationalization was supported by reacting 2 and 7 with DCl/D2O. Compou...
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| Veröffentlicht in: | Liebigs Annalen 1996-06, Vol.1996 (6), p.953-957 |
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| container_issue | 6 |
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| container_title | Liebigs Annalen |
| container_volume | 1996 |
| creator | Peseke, Klaus Aldinger, Stephan Reinke, Helmut |
| description | The treatment of the α‐oxoketene dithioacetal sugar derivatives 2 and 7 with concentrated hydrochloric acid in THF leads to the open‐chain uloses 3 and 8. The reaction mechanism can be rationalized as a retro‐aldol reaction. This rationalization was supported by reacting 2 and 7 with DCl/D2O. Compound 3 was converted into the chiral pyrazoles 12 and 13. The branched‐chain ulose 2 forms the thiopyranosidulose 15 when treated with diluted aqueous sulfuric acid in THF. The mechanism of this reaction was investigated by 13C‐labelling of the starting compound 2.
An Unusual C‐1‐‐C‐2 Ring‐Splitting of Pyranosides by a Retro‐Aldol Reaction – a Route to New Chiral Building Blocks |
| doi_str_mv | 10.1002/jlac.199619960614 |
| format | Article |
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An Unusual C‐1‐‐C‐2 Ring‐Splitting of Pyranosides by a Retro‐Aldol Reaction – a Route to New Chiral Building Blocks</description><identifier>ISSN: 0947-3440</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/jlac.199619960614</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>branched chain ; Carbohydrates ; Carbohydrates, branched chain ; Chiral building blocks ; open chain ; Push-pull alkenes ; Pyrazoles ; Retro-aldol reaction ; Uloses ; Uloses, open chain</subject><ispartof>Liebigs Annalen, 1996-06, Vol.1996 (6), p.953-957</ispartof><rights>Copyright © 1996 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3394-55b629cf1c58ce7aca278efe583d14da3f7c813f26b75f1e73929409eb64080a3</citedby><cites>FETCH-LOGICAL-c3394-55b629cf1c58ce7aca278efe583d14da3f7c813f26b75f1e73929409eb64080a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fjlac.199619960614$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjlac.199619960614$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Peseke, Klaus</creatorcontrib><creatorcontrib>Aldinger, Stephan</creatorcontrib><creatorcontrib>Reinke, Helmut</creatorcontrib><title>An Unusual C-1C-2 Ring-Splitting of Pyranosides by a Retro-Aldol Reaction - a Route to New Chiral Building Blocks</title><title>Liebigs Annalen</title><addtitle>Liebigs Ann./Recl</addtitle><description>The treatment of the α‐oxoketene dithioacetal sugar derivatives 2 and 7 with concentrated hydrochloric acid in THF leads to the open‐chain uloses 3 and 8. The reaction mechanism can be rationalized as a retro‐aldol reaction. This rationalization was supported by reacting 2 and 7 with DCl/D2O. Compound 3 was converted into the chiral pyrazoles 12 and 13. The branched‐chain ulose 2 forms the thiopyranosidulose 15 when treated with diluted aqueous sulfuric acid in THF. The mechanism of this reaction was investigated by 13C‐labelling of the starting compound 2.
An Unusual C‐1‐‐C‐2 Ring‐Splitting of Pyranosides by a Retro‐Aldol Reaction – a Route to New Chiral Building Blocks</description><subject>branched chain</subject><subject>Carbohydrates</subject><subject>Carbohydrates, branched chain</subject><subject>Chiral building blocks</subject><subject>open chain</subject><subject>Push-pull alkenes</subject><subject>Pyrazoles</subject><subject>Retro-aldol reaction</subject><subject>Uloses</subject><subject>Uloses, open chain</subject><issn>0947-3440</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><recordid>eNqFkEFOwzAURC0EEqVwAHa-gIsdJ068Qm0ELRAVKBTYWa7jgFsTV3Gq0vNwEI7EFUhUhBAbFl9_pNG8xQPgmOAewTg4mVupeoRz1h5mJNwBHYI5R5hxvAs6mIcxomGI98GB93OMMWeMdEDdL-G0XPmVtDBF5PP9I0UBnJjyGd0tranrJkFXwJtNJUvnTa49nG2ghBNdVw71be5sk6WqjSshagu3qjWsHRzrNUxfTNWQBytj85Y0sE4t_CHYK6T1-uj7d8H0_Ow-HaHseniR9jOkKOUhiqIZC7gqiIoSpWOpZBAnutBRQnMS5pIWsUoILQI2i6OC6JjygIeY6xkLcYIl7QKy5arKeV_pQiwr8yqrjSBYtNpEq0381tZsTrebtbF68_9AXGb99A8BbQnG1_rthyCrhWAxjSPxOB4K-pRdPYxubsWYfgGueoLT</recordid><startdate>199606</startdate><enddate>199606</enddate><creator>Peseke, Klaus</creator><creator>Aldinger, Stephan</creator><creator>Reinke, Helmut</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>199606</creationdate><title>An Unusual C-1C-2 Ring-Splitting of Pyranosides by a Retro-Aldol Reaction - a Route to New Chiral Building Blocks</title><author>Peseke, Klaus ; Aldinger, Stephan ; Reinke, Helmut</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3394-55b629cf1c58ce7aca278efe583d14da3f7c813f26b75f1e73929409eb64080a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>branched chain</topic><topic>Carbohydrates</topic><topic>Carbohydrates, branched chain</topic><topic>Chiral building blocks</topic><topic>open chain</topic><topic>Push-pull alkenes</topic><topic>Pyrazoles</topic><topic>Retro-aldol reaction</topic><topic>Uloses</topic><topic>Uloses, open chain</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Peseke, Klaus</creatorcontrib><creatorcontrib>Aldinger, Stephan</creatorcontrib><creatorcontrib>Reinke, Helmut</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Liebigs Annalen</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Peseke, Klaus</au><au>Aldinger, Stephan</au><au>Reinke, Helmut</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Unusual C-1C-2 Ring-Splitting of Pyranosides by a Retro-Aldol Reaction - a Route to New Chiral Building Blocks</atitle><jtitle>Liebigs Annalen</jtitle><addtitle>Liebigs Ann./Recl</addtitle><date>1996-06</date><risdate>1996</risdate><volume>1996</volume><issue>6</issue><spage>953</spage><epage>957</epage><pages>953-957</pages><issn>0947-3440</issn><eissn>1099-0690</eissn><abstract>The treatment of the α‐oxoketene dithioacetal sugar derivatives 2 and 7 with concentrated hydrochloric acid in THF leads to the open‐chain uloses 3 and 8. The reaction mechanism can be rationalized as a retro‐aldol reaction. This rationalization was supported by reacting 2 and 7 with DCl/D2O. Compound 3 was converted into the chiral pyrazoles 12 and 13. The branched‐chain ulose 2 forms the thiopyranosidulose 15 when treated with diluted aqueous sulfuric acid in THF. The mechanism of this reaction was investigated by 13C‐labelling of the starting compound 2.
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| ispartof | Liebigs Annalen, 1996-06, Vol.1996 (6), p.953-957 |
| issn | 0947-3440 1099-0690 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_jlac_199619960614 |
| source | Wiley Journals |
| subjects | branched chain Carbohydrates Carbohydrates, branched chain Chiral building blocks open chain Push-pull alkenes Pyrazoles Retro-aldol reaction Uloses Uloses, open chain |
| title | An Unusual C-1C-2 Ring-Splitting of Pyranosides by a Retro-Aldol Reaction - a Route to New Chiral Building Blocks |
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