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Non-Classical Epimerisation of (1S,2S,3S,4R,5R)-1-O-Methylcyclohexane-1,2,3,4,5-pentol

✍ Scribed by Michael Frank; Ralf Miethchen; Helmut Reinke

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
290 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

Methoxycyclitol 4 was acetalized in a non-classical one-pot idene moiety was realised in two steps via the corresponding ethylidene acetals 8 and 9; the ethylidene function was procedure with chloral/dicyclohexylcarbodiimide forming the 4-epi derivative 6. The stepwise deprotection of removed with aqueous trifluoroacetic acid (compound 10 from 6 via 9). Finally, the carbamoyl derivative 10 was compound 6 is also described. Thus, decarbamoylation to the acetal 7 was achieved by heating 6 with methanolic sodium converted into the tetra-O-acetyl product 12 via the tetrol 11. methoxide, and cleavage of the acid-stable trichloroethyl-[ ] Part 14: Ref.

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The condensation of (1 R,2S) or (lS,2S)-N,N'-dimethyI-l-phenylpropane-l 2-diamines with aldehydes gives respectively two diastereorneric 2-alkyl-l,3,4-trimethyI-S-phen limidazolidines. At thermodynamical equilibrium the major isomer in the erythro series is this one where t f ! e substituents at pos