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Structure and stereochemistry of 2-chloromethylpenam and 3-chlorocepham derivatives studied by 13c and 1h nmr spectroscopy

✍ Scribed by Kazuo Tori; Tadahiko Tsushima; Youko Tamura; Hiroko Shigemoto; Teruji Tsuji; Hiroyuki Ishitobi; Hiroshi Tanida

Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
230 KB
Volume
16
Category
Article
ISSN
0040-4039

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✦ Synopsis

During our investigation of conversion from penicillins to cephalosporins, we needed to assign three isomeric products, obtained fran the reaction in the preceding paper,' to the four possible structures, %, 2o-(3 and 28-chloro-substituted methyl phthalimidopenicillanates (a, and 3B-(2 and 3a-chloro-7Bphthalimidocephams (9. This problem has become important since previous workers2 seemed to assign incorrectly the 3-chlorocepham to 5_; at an earlier stage the structure and stereochemistry of these iscmers could not unambiguously be established readily by 'H NMR as well as other spectroscopies. Thus, we wish to report here our structural assessment of these compounds by 13C and 'H NMR spectroscopy. The natural-abundance 13C FT NMR spectra of methyl phthalimidopenicillanate (3, 3 3 2a,28-di-

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