Synthesis of a novel N-1 carbocyclic, N-9 butyl analogue of cyclic ADP ribose (cADPR)

被引：29

作者：

Galeone, A ^{[1
]}

Mayol, L ^{[1
]}

Oliviero, G ^{[1
]}

Piccialli, G ^{[1
]}

Varra, M ^{[1
]}

机构：

[1] Univ Naples Federico II, Dipartimento Chim Sostanze Nat, I-80131 Naples, Italy

来源：

TETRAHEDRON | 2002年 / 58卷 / 02期

关键词：

cADPR; pyrophosphate bond; cyclization;

D O I：

10.1016/S0040-4020(01)01162-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new analogue 1 of cADPR was prepared through a synthetic pathway starting from 6-chloropurine 2 which underwent two sequential alkylations at N-9 and N-1, with formation of the intermediate 8. The successive bis-phosphorylation of hydroxyalkyl functions, followed by deprotection and reprotection steps, afforded the derivative 13, the substrate for the cyclization reaction. This was carried out according to the Matsuda procedure and led to the intramolecular pyrophosphate bond formation, thus affording 14. The final deprotection of 14, in alkaline conditions, gave the target compound 1 in good yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：363 / 368

页数：6

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