Synthesis of chloro (diethylalkoxyphosphine) gold (I) salts and their subsequent conversion to s-diethylalkoxyphosphine gold 2,3,4,6-tetra-o-acetyl-thio-β-D-glucopyranosides

Das reaktive acetylgeschutzte 0-(a-D-Glucopyranosy1)trichloracetimidat 3 liefert mit S-Nucleophilen unter Bortrifluorid-Ether-Katalyse erwartungsgemll3 unter Inversion der Konfiguration ausschliel3lich 1-Thio-P-D-glucopyranoside. Mit dern entsprechenden benzylgeschiitzten a-Trichloracetirnidat 4 werden unter Retention der Konfiguration ausschliel3lich 1-Thio-a-D-glucopyranoside erhalten. Die Bedeutung von Alkyl-1-thio-B-o-galactopyranosiden zur Enzyminduktion war AnlaR, diese einfache Glycosylubertragung auch zur Synthese von Isopropyl-1-thio-P-Dgalactopyranosid (12a) und des Natriumsalzes von 1-Thio-P-D-galactopyranose (12b) anzuwenden. Glycosylimidates, 8 I). -Synthesis of 1-ThioglycosidesAs expected, the reactive acetyl-protected O-(a-D-glUCOpyranOSy1) trichloroacetimidate 3 reacts with S-nucleophiles and trifluoroborane-ether as catalyst to yield exclusively I-thio-P-D-glucopyranosides with inversion of the configuration. The corresponding benzyl-protected a-trichloroacetimidate 4 affords with retention of the configuration alkyl 1 -thio-a-D-glucopyranosides. The importance of alkyl I-thio-f3-D-galactopyranosides in enzyme induction was reason to apply this convenient and efficient glycosyl-transfer reaction to the synthesis of isopropyl 1-thi0-D-Dgalactopyranoside (12a) and the sodium salt of 1-thio-P-D-galactopyranose (12b), respectively.

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Synthesis of chloro (diethylalkoxyphosphine) gold (I) salts and their subsequent conversion to s-diethylalkoxyphosphine gold 2,3,4,6-tetra-o-acetyl-thio-β-D-glucopyranosides

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From Other Organophosphorus(III) Compounds by Substitution Reactions with Complexes of the Metals

From Other Organophosphorus(III) Compounds by Substitution Reactions with Complexes of the Metals

ChemInform Abstract: SYNTHESIS OF CHLORO(DIETHYLALKOXYPHOSPHINE)GOLD(I) SALTS AND THEIR SUBSEQUENT CONVERSION TO S‐DIETHYLALKOXYPHOSPHINEGOLD 2,3,4,6‐TETRA‐O‐ACETYL‐1‐THIO‐β‐D‐GLUCOPYRANOSIDES

Glycosylimidate, 8. Synthese von 1‐Thioglycosiden

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