Deoxygenation of 5-O-benzoyl-1,2-isopropylidene-3-O-imidazolylthiocarbonyl-α-D-xylofuranose using dimethyl phosphite:: an efficient alternate method towards a 3'-deoxynucleoside glycosyl donor

被引：3

作者：

Zlatev, Ivan ^{[1
,2
]}

Vasseur, Jean-Jacques ^{[1
,2
]}

Morvan, Francois ^{[1
,2
]}

机构：

[1] Univ Montpellier 1, CNRS, UMR 5247, IBMM, F-34095 Montpellier 5, France

[2] Univ Montpellier 2, CNRS, UMR 5247, IBMM, F-34095 Montpellier 5, France

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 20期

关键词：

3'-deoxynucleosides; Barton-McCombie deoxygenation; thiocarbonylimidazolyl; dimethyl phosphite;

D O I：

10.1016/j.tetlet.2008.03.079

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient radical deoxygenation reaction of thiocarbonylimidazolyl activated glycoside analogue using dimethyl phosphite as hydrogen source and radical chain carrier was performed as a key step in a multi step synthesis towards a common 3-deoxy glycosyl donor for 3'-deoxynucleosides. This method has safety and cost advantages compared to the generally used radical reduction reagents. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：3288 / 3290

页数：3

共 4 条

[1] CONVERSION OF 1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLOFURANOSE INTO 3-O-BENZOYL-5-BROMO AND -5-IODO-5-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLOFURANOSE VIA A CYCLIC N,N-DIMETHYLBENZAMIDE ACETAL DERIVATIVE
CULBERTS.TP
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (20): : 3624 - 3625
[2] [2+2]cycloaddition of chlorosulfonyl isocyanate to (Z)3-O-(2′-silylvinyl)ethers of 1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose
Lysek, R
Kaluza, Z
Furman, B
Chmielewski, M
TETRAHEDRON, 1998, 54 (46) : 14065 - 14080
[3] Hydroxy group interactions in stannylated carbohydrates.: Structures and thermal stabilities of 5-deoxy-5-C-(Ph3Sn)-1,2-O-isopropylidene-α-D-xylofuranose, 5-deoxy-5-C-(IPh2Sn)-1,2-O-isopropylidene-α-D- and -L-xylofuranose, and 5-deoxy-5-C(I2PhSn)-1,2-O-isopropylidene-α-D- and -L-xylofuranose
Burnett, LA
Ferreira, VF
Howie, RA
Rufino, H
Skakle, JMS
Wardell, JL
Wardell, SMSV
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (20): : 2288 - 2300
[4] APPROACHES TO THE STEREOSELECTIVE SYNTHESIS OF RING-AZAPROSTANOIDS .1. SYNTHESIS OF 3,4-BIS-(ACETAMIDO)-5-O-BENZOYL-3,4-DIDEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-XYLOFURANOSE, A CHIRAL PRECURSOR OF 7,11-DIAZAPROSTANOIDS
COETZEE, I
HOLZAPFEL, CW
KOEKEMOER, JM
VONPLATEN, AE
SOUTH AFRICAN JOURNAL OF CHEMISTRY, 1984, 37 (01) : 11 - 18

← 1 →