Synthesis of ld-Hepp and KDO containing di- and tetrasaccharide derivatives of Neisseria meningitidis inner-core region via iodonium ion promoted glycosidations

G. J.P.H. Boons; F. L. van Delft; P. A.M. van der Klein; G. A. van der Marel; J. H. van Boom

doi:10.1016/S0040-4020(01)88191-6

Synthesis of ld-Hepp and KDO containing di- and tetrasaccharide derivatives of Neisseria meningitidis inner-core region via iodonium ion promoted glycosidations

G. J.P.H. Boons^*
, F. L. van Delft
, P. A.M. van der Klein
, G. A. van der Marel
, J. H. van Boom

^*Corresponding author for this work

Leiden University
extern

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

Abstract

The synthesis of methyl(ethyl) 2-thio-KDO i.e. 1, 2, 5, 7 and 10 and ethyl 1-thio-ldHepp (i.e. 26 and 43 derivatives will be described. The latter derivatives proved to be suitable donors in iodonium ion (NIS/TfOH) promoted glycosidation reactions. The usefulness of the glycosidation approach was illustrated by the successful conclusion of a spacer containing dimer l-α-d-Hepp(1→5)-α-KDO-2-O-(CH₂)₃NH₂ (37) and tetramer β-d-Galp-(1→4)- β-dGlcp-(1→4)-l-α-d-Hepp(1→5)-α-KDO-2-O-(CH₂)₃NH₂ (47).

Original language	English
Pages (from-to)	885-904
Number of pages	20
Journal	Tetrahedron
Volume	48
Issue number	5
DOIs	https://doi.org/10.1016/S0040-4020(01)88191-6
Publication status	Published - 1 Jan 1992
Externally published	Yes

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@article{39c3ac301a75411bb15c490587b7a46b,

title = "Synthesis of ld-Hepp and KDO containing di- and tetrasaccharide derivatives of Neisseria meningitidis inner-core region via iodonium ion promoted glycosidations",

abstract = "The synthesis of methyl(ethyl) 2-thio-KDO i.e. 1, 2, 5, 7 and 10 and ethyl 1-thio-ldHepp (i.e. 26 and 43 derivatives will be described. The latter derivatives proved to be suitable donors in iodonium ion (NIS/TfOH) promoted glycosidation reactions. The usefulness of the glycosidation approach was illustrated by the successful conclusion of a spacer containing dimer l-α-d-Hepp(1→5)-α-KDO-2-O-(CH2)3NH2 (37) and tetramer β-d-Galp-(1→4)- β-dGlcp-(1→4)-l-α-d-Hepp(1→5)-α-KDO-2-O-(CH2)3NH2 (47).",

author = "Boons, \{G. J.P.H.\} and \{van Delft\}, \{F. L.\} and \{van der Klein\}, \{P. A.M.\} and \{van der Marel\}, \{G. A.\} and \{van Boom\}, \{J. H.\}",

year = "1992",

month = jan,

day = "1",

doi = "10.1016/S0040-4020(01)88191-6",

language = "English",

volume = "48",

pages = "885--904",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "5",

}

TY - JOUR

T1 - Synthesis of ld-Hepp and KDO containing di- and tetrasaccharide derivatives of Neisseria meningitidis inner-core region via iodonium ion promoted glycosidations

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

AU - van Delft, F. L.

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

AU - van der Marel, G. A.

AU - van Boom, J. H.

PY - 1992/1/1

Y1 - 1992/1/1

N2 - The synthesis of methyl(ethyl) 2-thio-KDO i.e. 1, 2, 5, 7 and 10 and ethyl 1-thio-ldHepp (i.e. 26 and 43 derivatives will be described. The latter derivatives proved to be suitable donors in iodonium ion (NIS/TfOH) promoted glycosidation reactions. The usefulness of the glycosidation approach was illustrated by the successful conclusion of a spacer containing dimer l-α-d-Hepp(1→5)-α-KDO-2-O-(CH2)3NH2 (37) and tetramer β-d-Galp-(1→4)- β-dGlcp-(1→4)-l-α-d-Hepp(1→5)-α-KDO-2-O-(CH2)3NH2 (47).

AB - The synthesis of methyl(ethyl) 2-thio-KDO i.e. 1, 2, 5, 7 and 10 and ethyl 1-thio-ldHepp (i.e. 26 and 43 derivatives will be described. The latter derivatives proved to be suitable donors in iodonium ion (NIS/TfOH) promoted glycosidation reactions. The usefulness of the glycosidation approach was illustrated by the successful conclusion of a spacer containing dimer l-α-d-Hepp(1→5)-α-KDO-2-O-(CH2)3NH2 (37) and tetramer β-d-Galp-(1→4)- β-dGlcp-(1→4)-l-α-d-Hepp(1→5)-α-KDO-2-O-(CH2)3NH2 (47).

UR - https://www.scopus.com/pages/publications/0026584780

U2 - 10.1016/S0040-4020(01)88191-6

DO - 10.1016/S0040-4020(01)88191-6

M3 - Article

AN - SCOPUS:0026584780

SN - 0040-4020

VL - 48

SP - 885

EP - 904

JO - Tetrahedron

JF - Tetrahedron

IS - 5

ER -

Synthesis of ld-Hepp and KDO containing di- and tetrasaccharide derivatives of Neisseria meningitidis inner-core region via iodonium ion promoted glycosidations

Abstract

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