A convenient, highly selective and eco-friendly N-Boc protection of pyrimidines under microwave irradiation

被引：10

作者：

Bessieres, Maxime ^{[1
]}

Roy, Vincent ^{[1
]}

Agrofoglio, Luigi A. ^{[1
]}

机构：

[1] Univ Orleans, ICOA, UMR CNRS 7311, Orleans, France

来源：

RSC ADVANCES | 2014年 / 4卷 / 104期

关键词：

EFFICIENT SYNTHESIS; TERT-BUTYLOXYCARBONYLATION; ACID; SOLVENT;

D O I：

10.1039/c4ra13033b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Protected pyrimidine nucleobases are of major importance as intermediates in the synthesis of nucleoside analogues and molecules with biological interests. We describe herein a novel practical microwave-assisted N-Boc protection of pyrimidine nucleobases under mild conditions using silica gel, avoiding treatment steps, and in increased yield.

引用

页码：59747 / 59749

页数：3

共 25 条

[1] Applications of diethoxymethane as a versatile process solvent and unique reagent in organic synthesis
Boaz, NW
Venepalli, B
[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (02) : 127 - 131
[2] Brown D.J., 1970, PYRIMIDINES
[3] Brown D. J., 1984, COMPREHENSIVE HETERO, V3, P84
[4] 9-FLUORENYLMETHOXYCARBONYL AMINO-PROTECTING GROUP
CARPINO, LA
HAN, GY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (22) : 3404 - &
[5] INSITU COMPLEXATION DIRECTS THE STEREOCHEMISTRY OF N-GLYCOSYLATION IN THE SYNTHESIS OF OXATHIOLANYL AND DIOXOLANYL NUCLEOSIDE ANALOGS
CHOI, WB
WILSON, LJ
YEOLA, S
LIOTTA, DC
SCHINAZI, RF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9377 - 9379
[6] Microwave assisted mild, rapid, solvent-less, and catalyst-free chemoselective N-tert-butyloxycarbonylation of amines
Dighe, Satish N.
Jadhav, Hemant R.
[J]. TETRAHEDRON LETTERS, 2012, 53 (43) : 5803 - 5806
[7] An efficient synthesis of a probe for protein function: 2,3-diaminopropionic acid with orthogonal protecting groups
Englund, EA
Gopi, HN
Appella, DH
[J]. ORGANIC LETTERS, 2004, 6 (02) : 213 - 215
[8] TOPICAL CHEMOTHERAPY WITH 5-FLUOROURACIL - A REVIEW
GOETTE, DK
[J]. JOURNAL OF THE AMERICAN ACADEMY OF DERMATOLOGY, 1981, 4 (06) : 633 - 649
[9] Green W., 1999, PROTECTIVE GROUPS OR
[10] Synthesis and broad spectrum antiviral evaluation of bis(POM) prodrugs of novel acyclic nucleosides
Hamada, Manabu
Roy, Vincent
McBrayer, Tamara R.
Whitaker, Tony
Urbina-Blanco, Cesar
Nolan, Steven P.
Balzarini, Jan
Snoeck, Robert
Andrei, Graciela
Schinazi, Raymond F.
Agrofoglio, Luigi A.
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 67 : 398 - 408

← 1 2 3 →