Matsuda–Heck Arylation of Glycals for the Stereoselective Synthesis of Aryl C‑Glycosides
The methoxymethyl-protected glycal l-amicetal, synthesized de novo from l-ethyl lactate through tandem ring-closing metathesis-isomerization sequence, undergoes a highly trans-diastereoselective Heck-type coupling reaction with various arene diazonium salts to furnish 2,3-unsaturated aryl C-glycosid...
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| Veröffentlicht in: | Journal of organic chemistry 2019-11, Vol.84 (22), p.14816-14829 |
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| container_title | Journal of organic chemistry |
| container_volume | 84 |
| creator | Otte, Fabian Schmidt, Bernd |
| description | The methoxymethyl-protected glycal l-amicetal, synthesized de novo from l-ethyl lactate through tandem ring-closing metathesis-isomerization sequence, undergoes a highly trans-diastereoselective Heck-type coupling reaction with various arene diazonium salts to furnish 2,3-unsaturated aryl C-glycosides in moderate to excellent yields. The products can be further functionalized, e.g., by hydrogenation, epoxidation, or dihydroxylation to furnish 2,3,6-tridesoxy, 2,3-anhydro-6-desoxy, or 6-desoxy aryl C-glycosides, respectively. The method was applied to the synthesis of an α-configured 6-desoxy-gliflozin derivative. |
| doi_str_mv | 10.1021/acs.joc.9b02410 |
| format | Article |
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The products can be further functionalized, e.g., by hydrogenation, epoxidation, or dihydroxylation to furnish 2,3,6-tridesoxy, 2,3-anhydro-6-desoxy, or 6-desoxy aryl C-glycosides, respectively. 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Org. Chem</addtitle><description>The methoxymethyl-protected glycal l-amicetal, synthesized de novo from l-ethyl lactate through tandem ring-closing metathesis-isomerization sequence, undergoes a highly trans-diastereoselective Heck-type coupling reaction with various arene diazonium salts to furnish 2,3-unsaturated aryl C-glycosides in moderate to excellent yields. The products can be further functionalized, e.g., by hydrogenation, epoxidation, or dihydroxylation to furnish 2,3,6-tridesoxy, 2,3-anhydro-6-desoxy, or 6-desoxy aryl C-glycosides, respectively. 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Org. Chem</addtitle><date>2019-11-15</date><risdate>2019</risdate><volume>84</volume><issue>22</issue><spage>14816</spage><epage>14829</epage><pages>14816-14829</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The methoxymethyl-protected glycal l-amicetal, synthesized de novo from l-ethyl lactate through tandem ring-closing metathesis-isomerization sequence, undergoes a highly trans-diastereoselective Heck-type coupling reaction with various arene diazonium salts to furnish 2,3-unsaturated aryl C-glycosides in moderate to excellent yields. The products can be further functionalized, e.g., by hydrogenation, epoxidation, or dihydroxylation to furnish 2,3,6-tridesoxy, 2,3-anhydro-6-desoxy, or 6-desoxy aryl C-glycosides, respectively. The method was applied to the synthesis of an α-configured 6-desoxy-gliflozin derivative.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>31615205</pmid><doi>10.1021/acs.joc.9b02410</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0002-0224-6069</orcidid></addata></record> |
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| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | ACS Publications |
| title | Matsuda–Heck Arylation of Glycals for the Stereoselective Synthesis of Aryl C‑Glycosides |
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