An improved synthesis of 1,2,3,4,6-Penta-O-Acetyl-5-Deoxy-5-C-[(R,S)-ethylphosphinyl]-α,β-d-glucopyranoses, and formation of 2,3,4,6-Tetra-O-acetyl-1,5-anhydro-5-deoxy-5-C-[(R)-Ethylphosphinyl]-d-glucitol
✍ Scribed by Hiroshi Yamamoto; Hiroshi Murata; Saburo Inokawa; Mitsuji Yamashita; Margaret-Ann Armour; Thomas T. Nakashima
- Publisher
- Elsevier Science
- Year
- 1984
- Tongue
- English
- Weight
- 417 KB
- Volume
- 133
- Category
- Article
- ISSN
- 0008-6215
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📜 SIMILAR VOLUMES
Various sugar analogs possessing a phosphorus atom in the hemiacetal ring have been preparedIe because of the interest in their physicochemical properties and also the potential utility of'their biological activity. Compared with a large number of the analogs having an alkyl-or aryl-phosphinyl group
5-Dcoxy-J,2-O-isopropylidene-S-C-(methoxyphenylphosphinyl)-~-O-~~thyl-n-D-ribofuranose (4) was prepared from 1,2-0-isopropylidene-3-O-methyl-a-D-ribo-pentodialdo-1,4-furanose by an addition reaction with methyl phenylphosphinate, followed by deoxygenation of the terminal HO-$H-P group of the adduct
We have previously reported' the synthesis of 1,2,3-tri-O-acetyGI,Sdideoxy-4-C-[(R,S)-phenylphosphinyl] -o&3-D-ribo-and -L-lyxo-furanoses (4) by the sequence of 1 -+ 2 + 3 + 4. However, this method could not be applied to a synthesis of 4deoxy-\*To whom correspondence may be addressed.