Synthesis of 1,2,3,4,6-penta-O-acetyl-5-deoxy-5-C-[(R)-ethylphosphinyl]-β-d-glucopyranose: A new route for preparation of d-glucopyranoses having phosphorus in the hemiacetal ring
✍ Scribed by Hiroshi Yamamoto; Keizo Yamamoto; Saburo Inokawa; Mitsuji Yamashita; Margaret-Ann Armour; Tom T. Nakashima
- Book ID
- 108308990
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- English
- Weight
- 156 KB
- Volume
- 102
- Category
- Article
- ISSN
- 0008-6215
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Treatment of 3-0-acetyl-5-deoxy-5-(dimethoxyphosphinyl)-l,2-O-isopropylidene-cr-D-glucofuranose (7) with dihydropyran in the presence of pyridinium ptoluenesulfonate gave the 6-0-(tetrahydropyran-2-yl) derivative in 91% yield. Ring-enlargement of this compound by the known, 2-step procedure gave 5-d
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.
X-ray crystallographic analyses are reported for the two title compounds (8 and 9), of which the former crystallized in two modifications (8n and 8b). In all three structures, the pyranose rings have the %, (D) conformation and the substituents at C-l are axial and those at C-24-4 are equatorial. Th