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Synthesis and Conformation of 1,1′-Biazetidinyl

✍ Scribed by Dr. Karl Kirste; Prof. Dr. Wolfgang Lüttke; Prof. Dr. Paul Rademacher

Publisher
John Wiley and Sons
Year
1978
Tongue
English
Weight
242 KB
Volume
17
Category
Article
ISSN
0044-8249

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✦ Synopsis

We have now investigated the reaction of TPA with compounds containing several hydroxyl groups in various configurations and of differing functionality; for example, the 9-(p-D-furanosy1)adenine derivatives ( I ) , ( ), (5), and (7).

According to Mitsunobu, reaction of adenosine ( I ) with TPA affords a 3',5'-pho~phorane[~'I. This structure is consistent with molecular models, and reactions with benzoic acid and thiobenzoic acid, which lead to the 5'-0-acyl derivatives.

We have repeated the reaction of (1) with TPA and confirmed the previously quoted melting point of the product[51. However, the NMR spectroscopic data favor the 2',3'-phosphorane structure ( ): a) The 'H-NMR spectrum ([D,]DMSO) shows a triplet at 6=5.2, which merges to a broad singlet on irradiation of the mean H5'", H5'b frequency and disappears on addition b) In the "P-NMR spectrum ([D,]DMSO) a signal is observed at 6= + 26.6 (standard: 85 % phosphoric acid), which lies in the region characteristic for triphenylphosphoranes. c) Decoupling experiments reveal P-H coupling with H2' and H 3 , but not with H5'" or H5'b.

d) The phosphorane (2) can be acylated with benzoyl chloride/pyridine to 5'-O-benzoyladenosine (3), which reacts with TPA to give the phosphorane ( 4 ) (31P-NMR: S=+26.5). of D20.

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