First synthesis of the β-D-rhamnosylated trisaccharide repeating unit of the O-antigen from Xanthomonas campestris pv. campestris 8004

被引：37

作者：

Bedini, E ^{[1
]}

Carabellese, A ^{[1
]}

Barone, G ^{[1
]}

Parrilli, M ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 20期

关键词：

D O I：

10.1021/jo051153d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The trisaccharide repeating unit of the O-antigen of the lipopolysaccharide from Xanthomonas campestris pv. campestris 8004, a pathogen of cruciferous crops, presents some structural features that renders it a challenging synthetic target: the presence of a beta-D-rhamnosidic linkage, the steric crowd on a 1,2-cis-diglycosylated D-rhamnose, and finally the noncommercial availability of its monosaccharide constituents. The synthesis of this trisaccharide as methyl glycoside has been accomplished by exploiting a strategy whose key steps were the sequential beta-D-rhamnosylation with a 2-O-benzylsulfonyl-N-phenyltrifluoroacetimidate donor, debenzylsulfonylation, and coupling with a D-Fucp3NAc thioglycoside donor.

引用

页码：8064 / 8070

页数：7

共 49 条

[1] Abdel-Rahman AAH, 2002, ANGEW CHEM INT EDIT, V41, P2972, DOI 10.1002/1521-3773(20020816)41:16<2972::AID-ANIE2972>3.0.CO
[2] 2-4
[3] Effect of dimethoxyethane in Yb(OTf)3-promoted glycosidations
Adinolfi, M
Iadonisi, A
Ravidà, A
Schiattarella, M
[J]. TETRAHEDRON LETTERS, 2004, 45 (23) : 4485 - 4488
[4] 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
[5] Aloui M, 2002, CHEM-EUR J, V8, P2608, DOI 10.1002/1521-3765(20020603)8:11<2608::AID-CHEM2608>3.0.CO
[6] 2-4
[7] A SYNTHESIS OF METHYL 3-O-(BETA-D-MANNOPYRANOSYL)-ALPHA-D-MANNOPYRANOSIDE FROM SULFONATE INTERMEDIATES
AWAD, LF
ELASHRY, ESH
SCHUERCH, C
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (05) : 1587 - 1592
[8] First synthesis of an α-D-Fucp3NAc containing oligosaccharide:: a study on D-Fucp3NAc glycosylation
Bedini, E
Carabellese, A
Schiattarella, M
Parrilli, M
[J]. TETRAHEDRON, 2005, 61 (23) : 5439 - 5448
[9] Structure-dependent modulation of a pathogen response in plants by synthetic O-antigen polysaccharides
Bedini, E
De Castro, C
Erbs, G
Mangoni, L
Dow, JM
Newman, MA
Parrilli, M
Unverzagt, C
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (08) : 2414 - 2416
[10] First preparative synthesis of a 3-acetamido-3,6-dideoxy-D-galactopyranose glycosyl donor via intramolecular cyclization of an epoxytrichloroacetimidate
Bedini, E
Iadonisi, A
Carabellese, A
Parrilli, M
[J]. TETRAHEDRON LETTERS, 2004, 45 (23) : 4445 - 4448

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