6-Deoxy-6-(dimethylphenylsilyl)-1,2:3,4-di-O-isopropylidene-β-l-altropyranose: Synthesis via hydrosilation, and reactivity
✍ Scribed by Joseph J. Pegram; Curtis B. Anderson
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- English
- Weight
- 165 KB
- Volume
- 184
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
Hydrosilation
of 5,6-unsaturated sugars is attractive as a method by which to prepare 6-C-silylated sugars. Such silylated sugars could serve as intermediates in reactions that exploit the unique reactivity of organosilanes, such as Petersen
📜 SIMILAR VOLUMES
The structures of the title compounds (2b and 3) have been investigated in the solid state by X-ray methods. The crystals of 2b are monoclinic, space group P2,, and of 3 orthorhombit, space grtup P2,2,2,. The cell dimensions are: for 2b, a = 9.910(2), b = 11;745W, c = 11.810(3) A, /3 = 97.32(l)"; a
Removal of the isopropylidene group under mild acidic conditions gave methyl 4-O-benzyl-6-deoxy-a-L-talopyranoside (3). Treatment of the dibutylstannylene derivative of compound 3 with benzyl bromide (2 equiv) and tetrabutylammonium bromide (1 equiv) in toluene afforded the 2-O-benzyl derivative 4 i
In the course of recent investigations '-4 in this series, we developed a oneflask synthesis of triacetalated, acyclic aldohexoses by use of 2,2-dialkoxypropanes or l,l-dialkoxycyclohexanes in the presence of p-toluenesulfonic acid. As shown in a preceding paper', one of the triacetals obtained from
3-0-(6-0-Acetyl-2,3-anhydro-4-deoxy-a-L-ribo-hexopyranosyl)-l,2:5,6-di-O-isopropylidene-a-D-glucofuranose has been synthesised and its monocrystal investigated by X-ray diffraction methods. The compound crystallises in the orthorhombic system, space group P2,2,2t, with cell constants a = 8.790( 7),