Premium
4‐Oxa(thia)‐9‐oxa‐2‐azabicyclo[4.2.1]nonane‐3‐on(thion) derivatives
Author(s) -
Škarić Vinko,
Hohnjec Marijan,
Škarić Djurdjica
Publication year - 1976
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19760590835
Subject(s) - chemistry , nonane , stereochemistry , sulfur , urea , medicinal chemistry , organic chemistry
The synthesis of 7,8‐dihydroxy‐2‐(2‐methoxycarbonylethyl)‐4,9‐dioxa‐2‐azabicyclo[4.2.1]nonane‐ 3‐thione ( 16 ) and of its parents 9‐oxa‐4‐thia‐3‐thione 17 , and 9‐oxa‐4‐thia‐3‐one 18 is described. The conversion of 5′‐deoxy‐5′‐iodo‐2′,3′‐ O, O ‐isopropylidene‐5,6‐dihydrouridin ( 1 ) into the 2‐ O ‐methyl‐5,6‐dihydrouridine 5 , the 5′‐ O ‐acetyl‐5,6‐dihydrouridine 4 , and into the N ‐(5‐ O ‐acetyl‐2,3‐ O, O ‐isopropylidene‐β‐ D ‐ribofuranosyl)‐ N ‐(2‐methoxycarbonyl thyl)‐urea ( 6 ) invoked 2′,3′‐ O, O ‐isopropylidene‐2,5′‐anhydro‐5,6‐dihydrouridine ( 2 ) as the common intermediate.