Peracetylated β-Allyl C-Glycosides of D-Ribofuranose and 2-Deoxy-D-ribofuranose in the Chemical Literature: Until Now, Mirages in the Literature

被引：7

作者：

Martinez, Heike Otero ^{[1
]}

Reinke, Helmut ^{[1
]}

Michalik, Dirk ^{[2
]}

Vogel, Christian ^{[1
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Univ Rostock, Leibniz Inst Catalysis, D-18059 Rostock, Germany

来源：

SYNTHESIS-STUTTGART | 2009年 / 11期

关键词：

allylation; glycosylation; C-glycosides; nucleosides; stereoselectivity; D-RIBOSE; NUCLEOSIDES; DERIVATIVES; ACID;

D O I：

10.1055/s-0029-1216794

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The peracetylated beta-allyl C-glycosides of D-ribofuranose (8) and 2-deoxy-D-ribofuranose (13) were stereoselectively prepared via the isopropylidene derivatives 3 and 4. These reactions represent what are, to the best of our knowledge, the first preparation of these apparently simple derivatives whose structures were carefully proved by NMR and X-ray investigations. Publications which allegedly described the synthesis of 8 and 13 were critically examined.

引用

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页码：1834 / 1840

页数：7

共 29 条

[1] A Versatile Approach to Alcohol, Aldehyde, Ketone and Amine Derivatives Starting from β-Allyl C-Glycosides of D-Ribofuranose and 2-Deoxy-D-ribofuranose
Waechtler, Heiko
Fuentes, Dilver Pena
Michalik, Dirk
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Kragl, Udo
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Vogel, Christian
SYNTHESIS-STUTTGART, 2011, (19): : 3099 - 3108
[2] SYNTHESIS OF 2-DEOXY-D-RIBOFURANOSE DERIVATIVES
MUKHANOV, VI
PREOBRAZ.MN
SUVOROV, NN
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[3] THE SYNTHESIS OF 2-DEOXY-D-RIBOFURANOSE 1-PHOSPHATE
MACDONALD, DL
FLETCHER, HG
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Hanaya, Tadashi
Tsukui, Hiroyuki
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Noguchi, Ayashi
Kawamoto, Heizan
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HETEROCYCLES, 2007, 72 : 411 - 420
[5] Synthesis of an aza analogue of 2-deoxy-D-ribofuranose and its homologues
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Pedersen, EB
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[6] 2-DEOXY-D-RIBOSE .8. SYNTHESIS OF ANOMERIC 2-DEOXY-D-RIBOFURANOSE 1-PHOSPHATES
MACDONALD, DL
FLETCHER, HG
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (07) : 1262 - &
[7] A convenient preparation of 1,2,3-tri-O-acetyl-β-D-ribofuranose by enzymatic regioselective 5-O-deacetylation of the peracetylated ribofuranose
Chien, TC
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[8] 1-Deoxy-1-(4-fluorophenyl)-β-D-ribofuranose, its hemihydrate, and 1-deoxy-1-(2,4-difluorophenyl)-β-D-ribofuranose: Structural evidence for intermolecular C-H···F-C interactions
Bats, Jan W.
Parsch, Joerg
Engels, Joachim W.
2000, Munksgaard Int Publ. Ltd., Copenhagen K, Denmark (56)
[9] 1-Deoxy-1-(4-fluorophenyl)-β-D-ribofuranose, its hemihydrate, and 1-deoxy-1-(2,4-difluorophenyl)-β-D-ribofuranose:: structural evidence for intermolecular C-H•••F-C interactions
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Bats, Jan W.
Parsch, Jorg
Engels, Joachim W.
Acta Crystallographica Section C: Crystal Structure Communications, 2000, 56 (02) : 201 - 205

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