Synthesis of 2,3-O-isopropylidene- and 3-O-benzoyl-2-O-benzyl-2-C-methyl-l-glyceraldehyde
โ Scribed by Masanori Yamaura; Tsuneji Suzuki; Yuji Tagami; Hironobu Hashimoto; Juji Yoshimura
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- English
- Weight
- 438 KB
- Volume
- 181
- Category
- Article
- ISSN
- 0008-6215
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โฆ Synopsis
2-C-Methylglyceraldehyde derivatives are among the simplest branchedchain chiral synthons and both the (R)-enantiomer and the (S)-enantiomer 'To whom correspondence should be addressed. *The temperature reported in ref. 4 must be revised.
๐ SIMILAR VOLUMES
Syntheses of the title glycosides are described. The critical O-glycosylations were carried out in the presence of boron trifluoride etherate with a high degree of alpha-selectivity.
D-Ribose was converted into methyl 5-O-benzyl-beta-D-ribofuranoside and this, on tin-mediated allylation, gave a mixture of the 2-O-allyl and 3-O-allyl derivatives which were separated by chromatography. The more polar isomer was characterised as the 3-O-allyl derivative after conversion via 3-O-all