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Synthesis of 4‐ β ‐D‐arabinofuranosyl‐5,6‐dihydro‐2 H ‐1,2,4‐thiadiazin‐3‐one 1,1‐dioxide and x‐ray diffraction analysis of its 2′,3‐anhydro precursor
Author(s) -
Schroeder A. C.,
Srikrishnan T.,
Parthasarathy R.,
Block A.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180327
Subject(s) - chemistry , sodium bicarbonate , ammonia , crystal structure , x ray crystallography , stereochemistry , sodium , crystallography , diffraction , nuclear chemistry , organic chemistry , physics , optics
Abstract Reaction of 2‐amino‐3′,5′‐bis( O‐tert ‐butyldimethylsilyl)‐β‐ D ‐arabinofuran[1′,2′:4,5]‐2‐oxazoline with 2‐chloroethylsulfonyl chloride in the presence of sodium bicarbonate followed by removal of the protecting groups gave 2′,3‐anhydro‐4‐β‐ D ‐arabinofuranosyl‐5,6‐dihydro‐2 H ‐1,2,4‐thiadiazin‐3‐one 1,1‐dioxide ( 5 ), which by treatment with ammonia was converted to 4‐β‐ D ‐arabinofuranosyl‐5,6‐dihydro‐2 H ‐1,2,4‐thiadiazin‐3‐one 1,1‐dioxide ( 6 ). The structure of compound 5 was unequivocally established by means of an x‐ray diffraction analysis. The compound crystallized in the space group P2 1 2 1 2 1 with unit cell dimensions a = 5.883(3), b = 9.352(2), c = 18.769(7) Å, Z = 4. Its structure was established by direct multisolution techniques and refined by the full matrix least squares method to a final R value of 0.058 for the 1515 reflections observed.