✦ LIBER ✦
Pummerer rearrangements and similar reactions of some six-membered cyclic sulphoxides: Synthesis of 3-deoxy-5-thiopentopyranoses branched at C-3
✍ Scribed by F. Santoyo Gonzalez; P. Garcia Mendoza; F.J. Lopez Aparicio
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- English
- Weight
- 913 KB
- Volume
- 183
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
Oxidation with 3-chloroperoxybenzoic acid of meso-3,5-diacetoxytetrahydrothiopyran derivatives 4,4_disubstituted variously with CO,Et, CN, Boc, and CONH, and 4-substituted with NO, gave mixtures of the corresponding sulphoxides 2a-e and 3a-e. These sulphoxides were converted by Pummerer rearrangement into 1,2,4-tri-O-acetyl-3-deoxy-5-thio-oL-pentopyranoses (4a-i) branched at C-3. Treatment of the sulphoxides with thionyl chloride gave 2,4-di-Oacetyl-3-deoxy-5-thio-DL-pentopyranosyl chlorides (4j-n) branched at C-3.