Versatile use of ytterbium(III) triflate and acid washed molecular sieves in the activation of glycosyl trifluoroacetimidate donors.: Assemblage of a biologically relevant tetrasaccharide sequence of Globo H

被引：41

作者：

Adinolfi, M ^{[1
]}

Iadonisi, A ^{[1
]}

Ravidà, A ^{[1
]}

Schiattarella, M ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 13期

关键词：

D O I：

10.1021/jo050301x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The nonreducing tetrasaccharide terminus of Globo H has been assembled in good yield and excellent stereocontrol exclusively by using mild and moisture stable agents such as Yb(OTf)3 and acid washed molecular sieves for the activation of glycosyltrifluoroacetimidate donors in the glycosylation steps. © 2005 American Chemical Society.

引用

页码：5316 / 5319

页数：4

共 30 条

[1] An easy and efficient approach for the installation of alkoxycarbonyl protecting groups on carbohydrate hydroxyls
Adinolfi, M
Barone, G
Guariniello, L
Iadonisi, A
[J]. TETRAHEDRON LETTERS, 2000, 41 (48) : 9305 - 9309
[2] Moisture stable promoters for selective α-fucosylation reactions:: Synthesis of antigen fragments
Adinolfi, M
Iadonisi, A
Ravidà, A
Schiattarella, M
[J]. SYNLETT, 2004, (02) : 275 - 278
[3] Efficient and direct synthesis of saccharidic 1,2-ethylidenes, orthoesters, and glycals from peracetylated sugars via the in situ generation of glycosyl iodides with I2/Et3SiH
Adinolfi, M
Iadonisi, A
Ravidà, A
Schiattarella, M
[J]. TETRAHEDRON LETTERS, 2003, 44 (43) : 7863 - 7866
[4] 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
[5] 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
[6] 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
[7] In vitro mimicry of CaMBr1 tumor-associated antigen by synthetic oligosaccharides
Adobati, E
Panza, L
Russo, G
Colnaghi, MI
Canevari, S
[J]. GLYCOBIOLOGY, 1997, 7 (02) : 173 - 178
[8] Allen JR, 2000, CHEM-EUR J, V6, P1366, DOI 10.1002/(SICI)1521-3765(20000417)6:8<1366::AID-CHEM1366>3.3.CO
[9] 2-B
[10] Synthesis of a versatile neuraminic acid "C"-disaccharide precursor for the synthesis of C-glycoside analogues of gangliosides
Bazin, HG
Du, YG
Polat, T
Linhardt, RJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19) : 7254 - 7259

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