Synthesis and conformational analysis of 6-[N,N-bis(dihydroxyphosphorylmethyl)amino]methyl-2-hydroxy-2-oxido-1,4,2-oxazaphosphorinane-4-methylphosphonic acid by NMR spectroscopy
- Authors: Bolt Y.V.1, Belus’ S.K.1, Tsirul’nikova N.V.1
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Affiliations:
- State Scientific-Research Institute of Chemical Reagents and High Purity Substances
- Issue: Vol 65, No 1 (2016)
- Pages: 291-294
- Section: Brief Communications
- URL: https://journals.rcsi.science/1066-5285/article/view/237072
- DOI: https://doi.org/10.1007/s11172-016-1300-8
- ID: 237072
Cite item
Abstract
The Kabachnik—Fields methylphosphorylation of 1,3-diaminopropan-2-ol affords a mixture of 1,3-diamino-2-hydroxypropane-N,N,N′,N′-tetrakismethylphosphonic acid and its intramolecular cyclic ester. Subsequent heating of this mixture led to the thermal dehydration of the acid with the 1,4,2-oxazaphosphorinane ring closure and the formation of 6-[N,N-bis(dihydroxyphosphorylmethyl)amino]methyl-2-hydroxy-2-oxido-1,4,2-oxazaphosphorinane4-methylphosphonic acid. A predominant chair conformation of the formed six-membered heterocycle was inferred from the data of 2D homonuclear (1H, 1H; J-resolved) and heteronuclear (1H, 13C; HSQC, HMBC) NMR correlation spectra.
About the authors
Ya. V. Bolt
State Scientific-Research Institute of Chemical Reagents and High Purity Substances
Author for correspondence.
Email: a1gol@icloud.com
Russian Federation, 3 ul. Bogorodsky val, Moscow, 107076
S. K. Belus’
State Scientific-Research Institute of Chemical Reagents and High Purity Substances
Email: a1gol@icloud.com
Russian Federation, 3 ul. Bogorodsky val, Moscow, 107076
N. V. Tsirul’nikova
State Scientific-Research Institute of Chemical Reagents and High Purity Substances
Email: a1gol@icloud.com
Russian Federation, 3 ul. Bogorodsky val, Moscow, 107076