Regio- and stereoselective synthesis of the carbocyclic analogue of 3-deoxy-β-D-manno-2-octulopyranosonic acid (β-KDO) from (-)-quinic acid.
✍ Scribed by H. Molin; B.G. Pring
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 215 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
REGIO-AND STEREOSELECTIVE SYNTHESIS OF TIE CARBOCYCLIC ANALOGlE OF 3-DEOXY-fl-D-MANNO-Z-OCTULOPYWOSONIC ACID (f34~0) w4 (-~QUINIC ACID.
📜 SIMILAR VOLUMES
Treatment of methyl 2,4,5,7,8-penta-O-acetyl-3-deoxy-cr-D-manno-oct-2ulopyranosonic acid, or its methyl ester, with refluxing methanolic O.lM hydrogen chloride for 16 h gave 95% of methyl (methyl 3-deoxy-a-D-manno-act-2-ulopyranosid)onate. Acetylation of the methyl ester of 3-deoxy-D-manno-act-2ulo
p-Acemxy-a4iaz.o esters yield a-en01 amate esters quantitatively by reaction with dirhodittm temmtate. The reaction was used to prepare tJte major natural cmtpounds 3-Deoxy-D-arabiio-2-Heptulosonic lrcid (DAH, 1) aud 3-Deoxy-D-manno-2-Cktulo.wnic