Synthesis of β-l-fucopyranosyl phosphate andl-fucofuranosyl phosphates by the MacDonald procedure
✍ Scribed by Harry S. Prihar; Tsai Ji-Hsiung; Steven R. Wanamaker; Stephanie J. Duber; Edward J. Bethrman
- Book ID
- 108308327
- Publisher
- Elsevier Science
- Year
- 1977
- Tongue
- English
- Weight
- 693 KB
- Volume
- 56
- Category
- Article
- ISSN
- 0008-6215
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A practical 15-mmol large-scale synthesis of beta-L-fucopyranosyl dicyclohexylammonium phosphate from L-fucose in 63% overall yield was developed. The synthesis took advantage of a neighboring Bz-2 group participating in a Koenigs-Knorr-like glycosylation. The sugar phosphate was transformed into th
## Abstract Reaction of the benzyl‐ and acetyl‐protected α‐trichloroacetimidates 1 and 6α with dialkyl and diaryl phosphates in the presence of traces of acid affords stereoelectively the thermodynamically more stable α‐L‐fucopyranosyl phosphates 2, 7 and 8, respectively, in high yields. The use of