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
| Autor: | Margaret-Ann Armour, Saburo Inokawa, Mitsuji Yamashita, Hiroshi Murata, Hiroshi Yamamoto, Thomas T. Nakashima |
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| Rok vydání: | 1984 |
| Předmět: |
chemistry.chemical_classification
biology Stereochemistry Sodium Organic Chemistry chemistry.chemical_element Hydrochloric acid General Medicine Nuclear magnetic resonance spectroscopy biology.organism_classification Biochemistry Analytical Chemistry chemistry.chemical_compound Acetic anhydride chemistry Aldose Yield (chemistry) Pyridine Tetra |
| Zdroj: | Carbohydrate Research. 133:45-51 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/0008-6215(84)85181-2 |
| Popis: | Treatment of 3- O -acetyl-5-deoxy-5- C -[ethyl(methoxy)phosphinyl]-1,2- O -isopropylidene-6- O -(triphenylmethyl)-α- d - xylo -hexofuranose conveniently prepared from 1,2:5,6-di- O -isopropylidene-α- d -glucose in 8 steps, with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by methanolic hydrochloric acid, and then acetic anhydride in pyridine, gave the title d -glucopyranoses in a higher overall yield than by the previous, alternative route. A minor amount of the title d -glucitol was also isolated, and characterized. Accurate 1 H-n.m.r. parameters for these ring-phosphorus-containing sugar analogs were obtained by the simulation analysis of their 400-MHz spectra. |
| Databáze: | OpenAIRE |
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