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Cyclophosphamides from aminosugars and aminonucleosides
Author(s) -
Fujiwara Allan N.,
Acton Edward M.,
Goodman Leon
Publication year - 1970
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.5570070423
Subject(s) - chemistry , diastereomer , condensation , stereochemistry , phosphorus , organic chemistry , physics , thermodynamics
Condensation of bis‐(2‐chloroethyl)phosphoramidic dichloride with 3′‐amino‐3′‐deoxy‐ N , N ‐dimethyladenosine afforded the 2′,3′‐cyclicphosphorodiamidate (III). By an improved synthesis, methyl 3‐amino‐3‐deoxy‐β‐D‐ribofuranoside was obtained as a model compound for conversion to the analogous 2,3‐cyclicphosphorodiamidate (XII). Existence of the latter as two diastereomers due to phosphorus asymmetry was shown by nmr analysis, using comparison with the 5‐( O ‐ p ‐nitrobenzoate) (XIII) as a basis for assignments.