Nucleophilic displacement reactions in carbohydrates: The formation of 1,4-anhydro-6-deoxy-2,3-O-isopropylidene-β-l-talopyranose (1,5-anhydro-6-deoxy-2,3-O-isopropylidene-α-l-talofuranose)
✍ Scribed by J.S. Brimacombe; L.C.N. Tucker
- Book ID
- 107725186
- Publisher
- Elsevier Science
- Year
- 1967
- Tongue
- English
- Weight
- 728 KB
- Volume
- 5
- Category
- Article
- ISSN
- 0008-6215
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📜 SIMILAR VOLUMES
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
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),
Several mono-and bi-cyclic polyhydroxylated alkaloids, isolated from plants', are specific and potent glycosidase inhibitors3, including those involved in the processing of glycoproteins4. Convenient intermediates for the synthesis of these compounds are 5-azido-5-deoxy sugar derivatives. Attempts