Studies on Pillaromycin A. III. The Structure of Pillarose
Pillarose (I), C8H12O5, gives positive Fehling's and iodoform reactions. Absorption of an isolated carbonyl is observed in the infrared and ultraviolet region. I formed methyl pillarosides (VIIa, b) and mono-, diacetylpillaroses, and reacted with sodium borohydride to yield methyl dihydropillar...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1970/09/25, Vol.18(9), pp.1713-1719 |
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| container_title | Chemical & pharmaceutical bulletin |
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| creator | ASAI, MITSUKO |
| description | Pillarose (I), C8H12O5, gives positive Fehling's and iodoform reactions. Absorption of an isolated carbonyl is observed in the infrared and ultraviolet region. I formed methyl pillarosides (VIIa, b) and mono-, diacetylpillaroses, and reacted with sodium borohydride to yield methyl dihydropillarosides (Xa, b). I consumed 2 moles of periodate. Periodate oxidation of I in acidic solution gave acetaldehyde, formic acid (and formaldehyde), succinaldehydic acid and carbon dioxide. From these degradation schemes and physico chemical properties of the above derivatives the structure, 2, 3, 6-trideoxy-2-glycoloylhexopyranos-4-ulose, was given to pillarose (I). |
| doi_str_mv | 10.1248/cpb.18.1713 |
| format | Article |
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III. The Structure of Pillarose</title><title>Chemical & pharmaceutical bulletin</title><addtitle>Chem. Pharm. Bull.</addtitle><description>Pillarose (I), C8H12O5, gives positive Fehling's and iodoform reactions. Absorption of an isolated carbonyl is observed in the infrared and ultraviolet region. I formed methyl pillarosides (VIIa, b) and mono-, diacetylpillaroses, and reacted with sodium borohydride to yield methyl dihydropillarosides (Xa, b). I consumed 2 moles of periodate. Periodate oxidation of I in acidic solution gave acetaldehyde, formic acid (and formaldehyde), succinaldehydic acid and carbon dioxide. 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The Structure of Pillarose</atitle><jtitle>Chemical & pharmaceutical bulletin</jtitle><addtitle>Chem. Pharm. Bull.</addtitle><date>1970</date><risdate>1970</risdate><volume>18</volume><issue>9</issue><spage>1713</spage><epage>1719</epage><pages>1713-1719</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><abstract>Pillarose (I), C8H12O5, gives positive Fehling's and iodoform reactions. Absorption of an isolated carbonyl is observed in the infrared and ultraviolet region. I formed methyl pillarosides (VIIa, b) and mono-, diacetylpillaroses, and reacted with sodium borohydride to yield methyl dihydropillarosides (Xa, b). I consumed 2 moles of periodate. Periodate oxidation of I in acidic solution gave acetaldehyde, formic acid (and formaldehyde), succinaldehydic acid and carbon dioxide. From these degradation schemes and physico chemical properties of the above derivatives the structure, 2, 3, 6-trideoxy-2-glycoloylhexopyranos-4-ulose, was given to pillarose (I).</abstract><cop>Tokyo</cop><pub>The Pharmaceutical Society of Japan</pub><doi>10.1248/cpb.18.1713</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| source | Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; Free Full-Text Journals in Chemistry |
| title | Studies on Pillaromycin A. III. The Structure of Pillarose |
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