Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents

被引：22

作者：

Gomez, Ana M. ^{[1
]}

Casillas, Marta ^{[1
]}

Barrio, Aitor ^{[1
]}

Gawel, Anna ^{[1
]}

Lopez, J. Cristobal ^{[1
]}

机构：

[1] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 23期

关键词：

glycosyl sulfoxides; organolithium reagents; pyranoid glycals; furanoid glycals; sulfoxide ligand exchange;

D O I：

10.1002/ejoc.200800318

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that undergoes beta-elimination of its C-2 substituent. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

引用

页码：3933 / 3942

页数：10

共 49 条

[1] Synthesis of furanoid and pyranoid C-1 aryl glycals by reaction of glycosyl chlorides with organolithium reagents
Gomez, Ana M.
Casillas, Marta
Rodriguez, Benjamin
Valverde, Serafin
Cristobal Lopez, J.
ARKIVOC, 2010, : 288 - 302
[2] A RAPID SYNTHESIS OF PYRANOID GLYCALS FROM GLYCOSYL BROMIDES
CAVALLARO, CL
SCHWARTZ, J
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (21): : 7055 - 7057
[3] A simple entry to pyranoid glycals: Reaction of anomeric glycosyl sulfoxides with organolithiums
Casillas, M
Gomez, AM
Lopez, JC
Valverde, S
SYNLETT, 1996, (07) : 628 - &
[4] The reactivity of furanoid and pyranoid glycals towards aromatic Grignard reagents and a nickel catalyst
Tingoli, M
Panunzi, B
Santacroce, F
TETRAHEDRON LETTERS, 1999, 40 (52) : 9329 - 9332
[5] ENOLATE CLAISEN REARRANGEMENT OF ESTERS FROM FURANOID AND PYRANOID GLYCALS
IRELAND, RE
THAISRIVONGS, S
VANIER, N
WILCOX, CS
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (01): : 48 - 61
[6] PREPARATION OF FURANOID AND PYRANOID GLYCALS FROM CARBOHYDRATE 1,2-DIOLS
HOLZAPFEL, CW
KOEKEMOER, JM
VERDOORN, GH
SOUTH AFRICAN JOURNAL OF CHEMISTRY, 1986, 39 (03) : 151 - 157
[7] A rapid synthesis of pyranoid glycals from glycosyl bromides (vol 60, pg 7056, 1995)
Cavallaro, CL
Schwartz, J
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (04): : 1554 - 1554
[8] NUCLEOSIDE SYNTHESIS FROM FURANOID GLYCALS
KAWAKAMI, H
EBATA, T
KOSEKI, K
OKANO, K
MATSUMOTO, K
MATSUSHITA, H
HETEROCYCLES, 1993, 36 (04) : 665 - 669
[9] CONVENIENT SYNTHESES OF SUBSTITUTED PYRANOID GLYCALS FROM THIOPHENYL GLYCOSIDES AND GLYCOSYL PHENYLSULFONES
FERNANDEZMAYORALAS, A
MARRA, A
TRUMTEL, M
VEYRIERES, A
SINAY, P
TETRAHEDRON LETTERS, 1989, 30 (19) : 2537 - 2540
[10] Synthesis of C-1 Alkyl and Aryl Glycals from Pyranosyl or Furanosyl Chlorides by Treatment with Organolithium Reagents
Gomez, Ana M.
Pedregosa, Ana
Casillas, Marta
Uriel, Clara
Cristobal Lopez, J.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (21) : 3579 - 3588

← 1 2 3 4 5 →