Regio- and stereospecific synthesis of dl-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol

[Display omitted] •The regio- and stereospecific synthesis of dl-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol.•Concise route to a chiro-inositol derivative ingluding bromine groups was developed.•Precursors of methoxy-, azido-, and aminoinostols were efficiently synthesized. The regio- and st...

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Bibliographic Details
Published in:Tetrahedron letters 2018-03, Vol.59 (13), p.1258-1260
Main Authors: Kelebekli, Latif, Aksu, Kadir, Şahin, Ertan
Format: Article
Language:English
Subjects:
chiro-Inositol
Methoxy conduritol-B
Methoxy inositol
Regio- and stereospecific synthesis
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Summary:[Display omitted] •The regio- and stereospecific synthesis of dl-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol.•Concise route to a chiro-inositol derivative ingluding bromine groups was developed.•Precursors of methoxy-, azido-, and aminoinostols were efficiently synthesized. The regio- and stereospecific synthesis of dl-4,5-dibromo-4,5-dideoxy-3,6-O-methyl-chiro-inositol is reported. Bromination of p-benzoquinone followed by reduction of the carbonyl groups with NaBH4 gave the corresponding trans-dibromodiol compound, which was reacted with sodium methoxide to produce dimethoxy conduritol-B. Regiospecific bromination of the alkene moiety furnished the desired chiro-inositol derivative.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.02.050