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

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