1,6-anhydro-3-O-benzyl-2-deoxy-2,4-di-C-methyl-β-d-hexopyranoses: Synthesis and properties
✍ Scribed by Alexander F. Sviridov; Michael S. Ermolenko; Dmitry V. Yashunsky; Alexander S. Shashkov; Nikolay K. Kochetkov
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- English
- Weight
- 1020 KB
- Volume
- 136
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
The synthesis of the isomeric 1,6-anhydro-3-0-benzyl-2-deoxy-2,4-di-Cmethyl-P-D-hexopyranoses and their spectral characterisation are described. 1,6-Anhydro-3-O-benzyl-2-deoxy-4-O-mesyl-2,4-di-C-methyl-~-D-galactopyranose undergoes ring-contraction on solvolysis.
📜 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
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