Nucleosides and nucleotides.: 191.: Ring expansion reaction of 1-[2,3,5-tri-O-TBS-4α-formyl-β-D-ribo-pentofuranosyl]uracil by treating with (methylene)triphenylphosphorane to give a new nucleoside containing dihydrooxepine ring at the sugar moiety

被引：7

作者：

Nomura, M

Endo, K

Shuto, S

Matsuda, A

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

[2] Taiho Pharmaceut Co Ltd, Hanno Res Ctr, Hanno, Saitama 3578527, Japan

来源：

TETRAHEDRON | 1999年 / 55卷 / 52期

关键词：

nucleosides; dihydrooxepine; ring-expansion; Wittig reactions;

D O I：

10.1016/S0040-4020(99)00968-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

When 1-[2,3,5-tri-O-TBS-4 alpha-formyl-beta-D-ribo-pentofuranosyl]uracil (5) was treated with (methylene)triphenylphosphorane in THF, an unusual ring-expansion reaction occurred to give a nucleoside (7) containing dihydrooxepine ring at the sugar moiety. A deuterium-label experiment showed that one carbon unit derived from the ylide was incorporated into the 5'-position of 7. A ring cleavage between the C-3' and C-4' of 5 during the reaction was suggested. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：14847 / 14854

页数：8