Synthesis of a cell wall component of Haemophilus (Actinobacillus) Pleuropneumoniae Serotype 5

P. A.M. van der Klein; W. Filemon; G. J.P.H. Boons; G. H. Veeneman; G. A. van der Marel; J. H. van Boom

doi:10.1016/S0040-4020(01)81239-4

Synthesis of a cell wall component of Haemophilus (Actinobacillus) Pleuropneumoniae Serotype 5

P. A.M. van der Klein^*
, W. Filemon
, G. J.P.H. Boons
, G. H. Veeneman
, G. A. van der Marel
, J. H. van Boom

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

The disaccharide α-d-GlcNacp-(1-5)-β-KDO-2-OCH₂CH₂CH₂NH₂ containing a spacer β-linked to KDO is prepared via iodonium ion-assisted glycosylation of a suitable KDO acceptor with ethyl 2-azido-2-deoxy-3,4-di-O-benzyl-1-thio-α/β-d-glucopyranoside. The key KDO building unit is synthesized in 7 steps starting with 2,3:5,6-di-O-isopropylidene-d-mannitol.

Original language	English
Pages (from-to)	4649-4658
Number of pages	10
Journal	Tetrahedron
Volume	48
Issue number	22
DOIs	https://doi.org/10.1016/S0040-4020(01)81239-4
Publication status	Published - 1 Jan 1992
Externally published	Yes

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@article{09870eec8b46455584b59351b547bd34,

title = "Synthesis of a cell wall component of Haemophilus (Actinobacillus) Pleuropneumoniae Serotype 5",

abstract = "The disaccharide α-d-GlcNacp-(1-5)-β-KDO-2-OCH2CH2CH2NH2 containing a spacer β-linked to KDO is prepared via iodonium ion-assisted glycosylation of a suitable KDO acceptor with ethyl 2-azido-2-deoxy-3,4-di-O-benzyl-1-thio-α/β-d-glucopyranoside. The key KDO building unit is synthesized in 7 steps starting with 2,3:5,6-di-O-isopropylidene-d-mannitol.",

author = "\{van der Klein\}, \{P. A.M.\} and W. Filemon and Boons, \{G. J.P.H.\} and Veeneman, \{G. H.\} and \{van der Marel\}, \{G. A.\} and \{van Boom\}, \{J. H.\}",

year = "1992",

month = jan,

day = "1",

doi = "10.1016/S0040-4020(01)81239-4",

language = "English",

volume = "48",

pages = "4649--4658",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "22",

}

TY - JOUR

T1 - Synthesis of a cell wall component of Haemophilus (Actinobacillus) Pleuropneumoniae Serotype 5

AU - van der Klein, P. A.M.

AU - Filemon, W.

AU - Boons, G. J.P.H.

AU - Veeneman, G. H.

AU - van der Marel, G. A.

AU - van Boom, J. H.

PY - 1992/1/1

Y1 - 1992/1/1

N2 - The disaccharide α-d-GlcNacp-(1-5)-β-KDO-2-OCH2CH2CH2NH2 containing a spacer β-linked to KDO is prepared via iodonium ion-assisted glycosylation of a suitable KDO acceptor with ethyl 2-azido-2-deoxy-3,4-di-O-benzyl-1-thio-α/β-d-glucopyranoside. The key KDO building unit is synthesized in 7 steps starting with 2,3:5,6-di-O-isopropylidene-d-mannitol.

AB - The disaccharide α-d-GlcNacp-(1-5)-β-KDO-2-OCH2CH2CH2NH2 containing a spacer β-linked to KDO is prepared via iodonium ion-assisted glycosylation of a suitable KDO acceptor with ethyl 2-azido-2-deoxy-3,4-di-O-benzyl-1-thio-α/β-d-glucopyranoside. The key KDO building unit is synthesized in 7 steps starting with 2,3:5,6-di-O-isopropylidene-d-mannitol.

UR - https://www.scopus.com/pages/publications/0026718546

U2 - 10.1016/S0040-4020(01)81239-4

DO - 10.1016/S0040-4020(01)81239-4

M3 - Article

AN - SCOPUS:0026718546

SN - 0040-4020

VL - 48

SP - 4649

EP - 4658

JO - Tetrahedron

JF - Tetrahedron

IS - 22

ER -

Synthesis of a cell wall component of Haemophilus (Actinobacillus) Pleuropneumoniae Serotype 5

Abstract

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