A new route to some enantiomerically pure substituted morpholines from d-ribono- and d-gulono-1,4-lactones
✍ Scribed by Khalil Bennis; Pierre Calinaud; Jacques Gelas; Mebrouk Ghobsi
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- English
- Weight
- 991 KB
- Volume
- 264
- Category
- Article
- ISSN
- 0008-6215
No coin nor oath required. For personal study only.
✦ Synopsis
o-Ribono-l,4-lactone, after acetalation, tritylation, and reduction, leads to a cyclization compound which gave with tosyl chloride 1,4-anhydro-2,3-O-isopropylidene-5-O-trityl-D-ribitol. The latter was transformed (acid hydrolysis, periodate oxidation, reduction, tritylation, and tosylation) into a ditosylated derivative 16, which was cyclized into morpholines by the action of primary amines. Acid hydrolysis, followed by acetylation, gives the (2s) -acetoxymethyl-4-isopropyltetrahydro-1,6oxazine (21). A similar sequence has been applied to D-gulonolactone to give access to oxazines 33,34, and 35.
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