A C-nucleoside derivative, 5-(5-deoxy-β-D-erythro-pent-4-enofuransyl)-1,3-dimethyluracil(33), which might be an important intermediate for transformations of pyrimidine ring and/or modifications of sugar moiety, was synthesized from pseudouridine via seven steps in 62% overall yield. Pseudouridine was sequentially 1,3-dimethylated, 2',3'-O-isopropylidenated, 5'-deoxy-5'-iodinated, deisopropylidenated, 2',3'-di-O-acylated, dehydroiodinated, and finally deacylated to yield the desired compound.
A derivative, 5-(3(R),4(R)-2,3- dihydroxy-4,5-epoxy-2,3-O-isopropylidene-1-penten-1-yl)-1,3- dimethyluracil(36) was obtained by treatment of 1,3-dimethyl-5-(2,3-O-isopropylidene-5-O-methanesulfonyl- β-D ribofuranosyl) uracil(34) with potassium tert-butoxide in dimethyl sulfoxide.
5-(5-Deoxy- 2,3-di-O-acetyl-β-D-erythro-pent-4-enofuranosyl)-1,3-dimethyluracil (32) was examined in the possibility of using it as an intermediate for the synthesis of other compounds by elimination or addition reactions.
C-뉴클레오사이드 유도체인 5-(5-데옥시-β-D-에리드로-펜트-4-에노푸라노실) -1, 3-디메틸우라실이 슈도우리딘으로 부터 7단계에 걸쳐서 전체수율 62%로 합성되었다. 이와 같은 화합물을 얻기 위해 슈도우리딘은 단계적으로 1, 3-디메틸화, 2', 3'-0-이소프로필리덴화, 5'-데옥시-5'-요드화, 탈이소프로필리덴화, 2', 3'-디-0-아실화, 탈수소요드화, 탈아실화 되었다. 이 화합물은 자체로서 중요성을 가질 뿐만 아니라, 여러 가지 유도체를 만들기 위한 중간체로 이용될 수 있을 것으로 예상된다.
4', 5'-불포화 C-뉴클레오사이드 유도체를 만드는 과정에서 광학이성체이며 비고리뉴클레오사이드 유도체인 5-(3 (R), 4(R)-2, 3-디히드록시-4, 5-에폭시-2, 3-0-이소프로필리덴-1-펜텐-1-일) -1, 3-디메틸우라실이 5'-0-메실 유도체로부터 만들어지는 것을 발견했다.
4', 5'-불포화 C-뉴클레오사이드 유도체인 5-(5-데옥시-2, 3-디-0-아세틸-β-D-에리드로-펜트-4-에노푸라노실) -1, 3-디메틸우라실의 반응성을 검토해 보았다.
