Synthetic studies of carbocyclic analogs of cyclic ADP-ribose.: Formation of a cyclic dimer, a 36-membered-ring product, in the condensation reaction of an 8-bromo-N1-[5-(phenylthiophosphoryl)carbocyclic-ribosyl]inosine 5′-phosphate derivative mediated by AgNO3

被引：15

作者：

Shuto, S ^{[1
]}

Shirato, M ^{[1
]}

Sumita, Y ^{[1
]}

Ueno, Y ^{[1
]}

Matsuda, A ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 40期

关键词：

nucleic acids analogues; cyclopentanes; phosphorylation; dimerisation;

D O I：

10.1016/S0040-4039(98)01575-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formation of symmetric 36-membered-ring product 14 was observed in the synthetic study of a stable mimic of cyclic ADP-ribose (cADPR, 1), When 8-bromo-N-1-[5-(phenylthiophosphoryl)carbocyclic-ribosyl]inosine 5'-phosphate derivative 5 was treated with AgNO3 and Et3N in N-methyl-2-pyrrolidinone-HMPA (3:1), the substrate was dimerized and cyclized to give 14 in 39% yield, (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7341 / 7344

页数：4

共 3 条

[1] Nucleosides and nucleotides part 187 -: Alternative synthesis of cyclic IDP-carbocyclic ribose.: Efficient cyclization of an 8-bromo-N1-[5-(phosphoryl)carbocyclic-ribosyl]inosine 5′-phenylthiophosphate derivative mediated by iodine
Fukuoka, M
Shuto, S
Minakawa, N
Ueno, Y
Matsuda, A
TETRAHEDRON LETTERS, 1999, 40 (29) : 5361 - 5364
[2] Nucleosides and nucleotides.: 173.: Synthesis of cyclic IDP-carbocyclic-ribose, a stable mimic of cyclic ADP-ribose.: Significant facilitation of the intramolecular condensation reaction of N-1-(carbocyclic-ribosyl)inosine 5′,6"-diphosphate derivatives by an 8-bromo-substitution at the hypoxanthine moiety
Shuto, S
Shirato, M
Sumita, Y
Ueno, Y
Matsuda, A
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06): : 1986 - 1994
[3] Nucleosides and Nucleotides. 173. Synthesis of Cyclic IDP-@carbocyclic-@ribose, a Stable Mimic of Cyclic ADP-@ribose. Significant Facilitation of the Intramolecular Condensation Reaction of N-@1-@(Carbocyclic-@ribosyl)inosine 5',6-@Diphosphate Derivatives by an 8-@Bromo-@Substitution at the Hypoxanthine Moiety
Shuto, S.
Shirato, M.
Sumita, Y.
Ueno, Y.
Journal of Organic Chemistry, 63 (06):

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