Sulfonate protecting groups.

ChemInform Abstract: The “Other” Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances in myo‐Inositol Chemistry)

“…[27] Thesynthesis of scyllo-inositol from myo-inositol via the orthoformate has been described (Scheme 12). [28] This synthesis illustrated that al arge amount of scyllo-inositol could be produced from inexpensive starting materials. myo-Inositol orthoformate (88)w as prepared without any chromatographic purification, then selectively benzoylated at the 2-hydroxy group to give 89.Tosylation of the 4-and 6-hydroxy groups gave 90 and selective debenzoylation gave the 2hydroxy derivative 91.S wern oxidation gave the ketone 92, which was reduced with sodium borohydride to provide the scyllo-inositol derivative 93 in excellent yield.…”

“…However,e poxidation of the Cd erivative 12 gave am ixture of epoxides 21 and 22,w hile the Fd erivative 15 gave amixture of epoxides 25 and 26.The epoxide derivatives 21 and 22 were subjected to acidic hydrolysis to provide racemic 1,2,3,6-tetra-O-benzyl-allo-inositol (23)a nd racemic 1,2,3,4-tetra-O-benzyl-myo-inositol (24). Ring opening of epoxides 25 and 26 under acidic conditions gave racemic 1,2,5,6-tetra-O-benzyl-muco-inositol (27)and racemic 2,3,4,5tetra-O-benzyl-myo-inositol (28). Further deprotection of these derivatives was not discussed;h owever,s imple hydrogenation in the presence of apalladium on carbon catalyst will give the respective inositols in high yield.…”

The “Other” Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances inmyo‐Inositol Chemistry)

“…[28] This synthesis illustrated that a large amount of scyllo-inositol could be produced from inexpensive starting materials. myo-Inositol orthoformate (88) was prepared without any chromatographic purification then selectively benzoylated at the 2-hydroxyl to give 89.…”

Die “anderen” Inositole und ihre Phosphate: Synthese, Biologie und Medizin (sowie jüngste Fortschritte in dermyo‐Inositolchemie)

“…Aus dem Conduritol-B-Derivat 17 entstand in hoher Ausbeute das Epoxid 18,d as mit Säure zum racemischen 1,4,5,6-Tetra-O-benzylchiro-inositol (19)u nd zum racemischen 1,2,3,4-Tetra-Obenzyl-scyllo-inositol (20)g eçffnet wurde.D emgegenüber entstand bei der Epoxidierung der Derivate von C( 12)e in Gemisch der Epoxide 21 und 22;a us F( 15)r esultierte das Epoxidgemisch aus 25 und 26.Die Epoxidderivate 21 und 22 wurden sauer zu racemischem 1,2,3,6-Tetra-O-benzyl-alloinositol (23)u nd racemischem 1,2,3,4-Tetra-O-benzyl-myoinositol (24)hydrolysiert. Die saure Ringçffnung der Epoxide 25 und 26 lieferte racemisches 1,2,5,6-Tetra-O-benzyl-mucoinositol (27)u nd racemisches 2,3,4,5-Tetra-O-benzyl-myoinositol (28). Die nachfolgende Abspaltung der Schutzgruppen von diesen Derivaten wird nicht diskutiert, weil durch einfache Hydrierung in Gegenwart von Palladium auf Kohle (32) und mit Tr ifluormethansulfonsäure-Anhydrid zum Zwischenprodukt 33 umgesetzt.…”

“…[27] Die Synthese von scyllo-Inositol aus myo-Inositol über Orthoformiat wurde bereits beschrieben (Schema 12). [28] Dieser Syntheseweg macht deutlich, dass große Mengen an scyllo-Inositol aus preisgünstigen Ausgangsverbindungen hergestellt werden kçnnen. myo-Inositolorthoformiat…”