Moisture stable promoters for selective α-fucosylation reactions:: Synthesis of antigen fragments

被引：21

作者：

Adinolfi, M ^{[1
]}

Iadonisi, A ^{[1
]}

Ravidà, A ^{[1
]}

Schiattarella, M ^{[1
]}

机构：

[1] Univ Naples Federico II, Dipartimento Chim Organ & Biochim, I-80126 Naples, Italy

来源：

SYNLETT | 2004年 / 02期

关键词：

carbohydrates; synthesis of oligosaccharides; stereo-selectivity in fucosylation reactions; acid-washed molecular sieves; ytterbium triflate;

D O I：

10.1055/s-2004-815415

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Moisture stable reagents Yb(OTf)(3) and acid washed molecular sieves (AW 300 MS) can act as mild promoters for selective alpha-fucosylation reactions. Using a combination of Yb(OTf)(3) and AW 300 MS a good stereocontrol is achieved with a perbenzylated fucosyl N-phenyl trifluoroacetimidate donor by exploiting the directing effect of ether solvents. With the AW 300 MS alone the selectivity can be obtained with partially acetylated donors by exploiting a long-range participation effect. Both systems proved suitable for the synthesis of fragments contained in important antigen sequences, included the Lewis X trisaccharide.

引用

页码：275 / 278

页数：4

共 46 条

[1] An approach to the highly stereocontrolled synthesis of α-glycosides.: Compatible use of the very acid labile dimethoxytrityl protecting group with Yb(OTf)3-promoted glycosidation
Adinolfi, M
Iadonisi, A
Schiattarella, M
[J]. TETRAHEDRON LETTERS, 2003, 44 (34) : 6479 - 6482
[2] Activation of glycoyl trihaloacetimidates with acid-washed molecular sieves in the glycosidation reaction
Adinolfi, M
Barone, G
Iadonisi, A
Schiattarella, M
[J]. ORGANIC LETTERS, 2003, 5 (07) : 987 - 989
[3] Efficient activation of glycosyl N-(phenyl)trifluoroacetimidate donors with ytterbium(III) triflate in the glycosylation reaction
Adinolfi, M
Barone, G
Iadonisi, A
Schiattarella, M
[J]. TETRAHEDRON LETTERS, 2002, 43 (32) : 5573 - 5577
[4] Activation of disarmed 2-O-alkoxycarbonylated glycosyl trichloroacetimidates with lanthanide triflates:: an efficient approach for the synthesis of 1,2-trans glycosides
Adinolfi, M
Barone, G
Iadonisi, A
Mangoni, L
Schiattarella, M
[J]. TETRAHEDRON LETTERS, 2001, 42 (34) : 5967 - 5969
[5] First total synthesis of α-(2 → 3)/α-(2 → 6)-disialyl lactotetraosyl ceramide and disialyl Lewis A ganglioside as cancer-associated carbohydrate antigens
Ando, T
Ishida, H
Kiso, M
[J]. CARBOHYDRATE RESEARCH, 2003, 338 (06) : 503 - 514
[6] SYNTHESIS OF GLYCOSIDES OF FUCOSE UNDER NEUTRAL CONDITIONS IN SOLUTIONS OF LICLO4 IN ORGANIC-SOLVENTS
BOHM, G
WALDMANN, H
[J]. TETRAHEDRON LETTERS, 1995, 36 (22) : 3843 - 3846
[7] SYNTHESES OF PARA-TRIFLUOROACETAMIDOPHENYL 3-O-[2-ACETAMIDO-2-DEOXY-3-O-(ALPHA-L-FUCOPYRANOSYL)-BETA-D-GLUCOPYRANOSYL]-BETA-D-GALACTOPYRANOSIDE AND OF PARA-TRIFLUOROACETAMIDOPHENYL 3-O-[2-ACETAMIDO-2-DEOXY-3-O-(ALPHA-L-FUCOPYRANOSYL)-4-O-(BETA-D-GALACTOPYRANOSYL)-BETA-D-GLUCOPYRANOSYL]-BETA-D-GALACTOPYRANOSIDE, A TRISACCHARIDE AND A TETRASACCHARIDE FRAGMENT OF THE LEX TUMOR-ASSOCIATED ANTIGENY
CLASSON, B
GAREGG, PJ
HELLAND, AC
[J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (04) : 543 - 551
[8] Stereoselective chemical 1,2-cis O-glycosylation:: From 'sugar ray' to modern techniques of the 21st century
Demchenko, AV
[J]. SYNLETT, 2003, (09) : 1225 - 1240
[9] A high yielding chemical synthesis of sialyl Lewis x tetrasaccharide and Lewis x trisaccharide; Examples of regio- and stereodifferentiated glycosylations
Ellervik, U
Magnusson, G
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) : 9314 - 9322
[10] Ernst B., 2000, CARBOHYD CHEM-SPR

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